TY  - JOUR
AU  - Andrić, Deana B.
AU  - Dukić-Stefanović, Slađana
AU  - Krunić, Mihajlo J.
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena Z.
AU  - Šukalović, Vladimir B.
AU  - Kostić-Rajačić, Slađana
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6472
AB  - Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most
noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-
coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors
treat central nervous system diseases such as schizophrenia and depression.
Recent advances in serotonin receptor structure research gave us several
crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic
drug aripiprazole (Abilify®). This discovery prompted us to evaluate
a series of newly synthesized ligands for serotonergic activity since those arylpiperazine
derivatives share minimal general structure with aripiprazole. The
results of molecular docking analysis of unsubstituted starting substances
encouraged us to propound further modifications of the tail and head parts of
the parent molecules to maximize receptor binding affinity. Intrigued by the
results of molecular analysis, all foreseen derivatives were synthesized. The
pharmacological activity of all nine (5a and 6a are synthesized previously)
compounds was assessed by the in vitro tests and in silico pharmacokinetics
predictions for the most promising candidates. All tested ligands have improved
affinity compering to parent compounds (10a and 11a), 8b and 9b expressed
the best pharmacological profile with an improved binding affinity
toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively).
PB  - Belgrade : Serbian Chemical Society
T2  - J. Serb. Chem. Soc.
T1  - Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides
VL  - 89
IS  - 3
SP  - 291
EP  - 303
DO  - 10.2298/JSC230906076A
ER  - 

@article{
author = "Andrić, Deana B. and Dukić-Stefanović, Slađana and Krunić, Mihajlo J. and Jevtić, Ivana I. and Penjišević, Jelena Z. and Šukalović, Vladimir B. and Kostić-Rajačić, Slađana",
year = "2024",
abstract = "Serotonin, or 5-hydroxytryptamine (5-HT), is a biogenic amine most
noted as a neurotransmitter, an activator of the utmost subtype family of G-protein-
coupled receptors (GPCR). Drugs targeting 5-HT1A and other 5-HT receptors
treat central nervous system diseases such as schizophrenia and depression.
Recent advances in serotonin receptor structure research gave us several
crystal 5-HT1A receptor structures, most notably 5-HT1A bound to the antipsychotic
drug aripiprazole (Abilify®). This discovery prompted us to evaluate
a series of newly synthesized ligands for serotonergic activity since those arylpiperazine
derivatives share minimal general structure with aripiprazole. The
results of molecular docking analysis of unsubstituted starting substances
encouraged us to propound further modifications of the tail and head parts of
the parent molecules to maximize receptor binding affinity. Intrigued by the
results of molecular analysis, all foreseen derivatives were synthesized. The
pharmacological activity of all nine (5a and 6a are synthesized previously)
compounds was assessed by the in vitro tests and in silico pharmacokinetics
predictions for the most promising candidates. All tested ligands have improved
affinity compering to parent compounds (10a and 11a), 8b and 9b expressed
the best pharmacological profile with an improved binding affinity
toward serotonin 5-HT1A receptors (Ki 12.1 and 4.8 nM, respectively).",
publisher = "Belgrade : Serbian Chemical Society",
journal = "J. Serb. Chem. Soc.",
title = "Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides",
volume = "89",
number = "3",
pages = "291-303",
doi = "10.2298/JSC230906076A"
}

Andrić, D. B., Dukić-Stefanović, S., Krunić, M. J., Jevtić, I. I., Penjišević, J. Z., Šukalović, V. B.,& Kostić-Rajačić, S.. (2024). Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides. in J. Serb. Chem. Soc.
Belgrade : Serbian Chemical Society., 89(3), 291-303.
https://doi.org/10.2298/JSC230906076A

Andrić DB, Dukić-Stefanović S, Krunić MJ, Jevtić II, Penjišević JZ, Šukalović VB, Kostić-Rajačić S. Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides. in J. Serb. Chem. Soc.. 2024;89(3):291-303.
doi:10.2298/JSC230906076A .

Andrić, Deana B., Dukić-Stefanović, Slađana, Krunić, Mihajlo J., Jevtić, Ivana I., Penjišević, Jelena Z., Šukalović, Vladimir B., Kostić-Rajačić, Slađana, "Synthesis, computational and pharmacological evaluation of novel N-{4-[2-(4-aryl-piperazin-1-yl)ethyl]phenyl}-arylamides" in J. Serb. Chem. Soc., 89, no. 3 (2024):291-303,
https://doi.org/10.2298/JSC230906076A . .

TY  - JOUR
AU  - Šegan, Sandra
AU  - Krunić, Mihajlo J.
AU  - Andrić, Deana B.
AU  - Šukalović, Vladimir B.
AU  - Penjišević, Jelena Z.
AU  - Jevtić, Ivana I.
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6473
AB  - Fourteen donepezil-like acetylcholinesterase (AChE) inhibitors from our library were
analyzed using reversed-phase thin-layer chromatography to assess their lipophilicity
and blood–brain barrier permeability. Compounds possessed N-benzylpiperidine and
N,N-diarylpiperazine moieties connected via a short carboxamide or amine linker.
Retention parameters RM
0, b, and C0 were considered as the measures of lipophilicity.
Besides, logD of the investigated compounds was determined chromatographically
using standard compounds with known logPow and logD values at pH 11. Experimentally
obtained lipophilicity parameters correlated well with in silico generated results,
and the effect of the nature of the linker between two pharmacophores and
substituents on the arylpiperazine part of the molecule was observed. As a result of
drug-likeness analysis, both Lipinski's rule of five and Veber's rule parameters were
determined, suggesting that examined compounds could be potential candidates for
further drug development. Principal component analysis was performed to obtain an
insight into a grouping of compounds based on calculated structural descriptors,
experimentally obtained values of lipophilicity, and AChE inhibitory activity.
PB  - Wiley
T2  - Biomedical Chromatography
T1  - Evaluation of lipophilicity and drug-likeness of donepezil-like compounds using reversed-phase thin-layer chromatography
VL  - n/a
SP  - e5864
DO  - 10.1002/bmc.5867
ER  - 

@article{
author = "Šegan, Sandra and Krunić, Mihajlo J. and Andrić, Deana B. and Šukalović, Vladimir B. and Penjišević, Jelena Z. and Jevtić, Ivana I.",
year = "2024",
abstract = "Fourteen donepezil-like acetylcholinesterase (AChE) inhibitors from our library were
analyzed using reversed-phase thin-layer chromatography to assess their lipophilicity
and blood–brain barrier permeability. Compounds possessed N-benzylpiperidine and
N,N-diarylpiperazine moieties connected via a short carboxamide or amine linker.
Retention parameters RM
0, b, and C0 were considered as the measures of lipophilicity.
Besides, logD of the investigated compounds was determined chromatographically
using standard compounds with known logPow and logD values at pH 11. Experimentally
obtained lipophilicity parameters correlated well with in silico generated results,
and the effect of the nature of the linker between two pharmacophores and
substituents on the arylpiperazine part of the molecule was observed. As a result of
drug-likeness analysis, both Lipinski's rule of five and Veber's rule parameters were
determined, suggesting that examined compounds could be potential candidates for
further drug development. Principal component analysis was performed to obtain an
insight into a grouping of compounds based on calculated structural descriptors,
experimentally obtained values of lipophilicity, and AChE inhibitory activity.",
publisher = "Wiley",
journal = "Biomedical Chromatography",
title = "Evaluation of lipophilicity and drug-likeness of donepezil-like compounds using reversed-phase thin-layer chromatography",
volume = "n/a",
pages = "e5864",
doi = "10.1002/bmc.5867"
}

Šegan, S., Krunić, M. J., Andrić, D. B., Šukalović, V. B., Penjišević, J. Z.,& Jevtić, I. I.. (2024). Evaluation of lipophilicity and drug-likeness of donepezil-like compounds using reversed-phase thin-layer chromatography. in Biomedical Chromatography
Wiley., n/a, e5864.
https://doi.org/10.1002/bmc.5867

Šegan S, Krunić MJ, Andrić DB, Šukalović VB, Penjišević JZ, Jevtić II. Evaluation of lipophilicity and drug-likeness of donepezil-like compounds using reversed-phase thin-layer chromatography. in Biomedical Chromatography. 2024;n/a:e5864.
doi:10.1002/bmc.5867 .

Šegan, Sandra, Krunić, Mihajlo J., Andrić, Deana B., Šukalović, Vladimir B., Penjišević, Jelena Z., Jevtić, Ivana I., "Evaluation of lipophilicity and drug-likeness of donepezil-like compounds using reversed-phase thin-layer chromatography" in Biomedical Chromatography, n/a (2024):e5864,
https://doi.org/10.1002/bmc.5867 . .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Suručić, Relja V.
AU  - Tovilović-Kovačević, Gordana
AU  - Zogović, Nevena
AU  - Kostić-Rajačić, Sladjana V.
AU  - Andrić, Deana
AU  - Penjišević, Jelena Z.
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6446
AB  - Simple and scalable synthetic approach was used for the preparation of thirteen novel tacrine derivatives consisting
of tacrine and N-aryl-piperidine-4-carboxamide moiety connected by a five-methylene group linker. An
anti-Alzheimer disease (AD) potential of newly designed tacrine derivatives was evaluated against two important
AD targets, acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). In vitro pharmacological evaluation
showed strong ChE inhibitory activity of all compounds, with IC50 values ranging from 117.5 to 455 nM for AChE
and 34 to 324 nM for BuChE. As a representative of the series with the best cytotoxicity / ChE inhibitory activity
ratio, expressed as the selectivity index (SI), 2-chlorobenzoyl derivative demonstrated mixed-type inhibition on
AChE and BuChE, suggesting binding to both CAS and PAS of the enzymes. It also exhibited antioxidant capacity
and neuroprotective potential against amyloid-β (Aβ) toxicity in the culture of neuron-like cells. In-depth
computational analysis corroborated well with in vitro ChE inhibition, illuminating that all compounds exhibit
significant potential in targeting both enzymes. Molecular dynamics (MD) simulations revealed that 2-chlorobenzoyl
derivative, created complexes with AChE and BuChE that demonstrated sufficient stability throughout the
observed MD simulation. Computationally predicted ADME properties indicated that these compounds should
have good blood–brain barrier (BBB) permeability, an important factor for CNS-targeting drugs. Overall, all
tested compounds showed promising pharmacological behavior, highlighting the multi-target potential of 2-
chlorobenzoyl derivative which should be further investigated as a new lead in the drug development process.
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry
T1  - Multi-target potential of newly designed tacrine-derived cholinesterase inhibitors: Synthesis, computational and pharmacological study
VL  - 101
SP  - 117649
DO  - 10.1016/j.bmc.2024.117649
ER  - 

@article{
author = "Jevtić, Ivana I. and Suručić, Relja V. and Tovilović-Kovačević, Gordana and Zogović, Nevena and Kostić-Rajačić, Sladjana V. and Andrić, Deana and Penjišević, Jelena Z.",
year = "2024",
abstract = "Simple and scalable synthetic approach was used for the preparation of thirteen novel tacrine derivatives consisting
of tacrine and N-aryl-piperidine-4-carboxamide moiety connected by a five-methylene group linker. An
anti-Alzheimer disease (AD) potential of newly designed tacrine derivatives was evaluated against two important
AD targets, acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). In vitro pharmacological evaluation
showed strong ChE inhibitory activity of all compounds, with IC50 values ranging from 117.5 to 455 nM for AChE
and 34 to 324 nM for BuChE. As a representative of the series with the best cytotoxicity / ChE inhibitory activity
ratio, expressed as the selectivity index (SI), 2-chlorobenzoyl derivative demonstrated mixed-type inhibition on
AChE and BuChE, suggesting binding to both CAS and PAS of the enzymes. It also exhibited antioxidant capacity
and neuroprotective potential against amyloid-β (Aβ) toxicity in the culture of neuron-like cells. In-depth
computational analysis corroborated well with in vitro ChE inhibition, illuminating that all compounds exhibit
significant potential in targeting both enzymes. Molecular dynamics (MD) simulations revealed that 2-chlorobenzoyl
derivative, created complexes with AChE and BuChE that demonstrated sufficient stability throughout the
observed MD simulation. Computationally predicted ADME properties indicated that these compounds should
have good blood–brain barrier (BBB) permeability, an important factor for CNS-targeting drugs. Overall, all
tested compounds showed promising pharmacological behavior, highlighting the multi-target potential of 2-
chlorobenzoyl derivative which should be further investigated as a new lead in the drug development process.",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry",
title = "Multi-target potential of newly designed tacrine-derived cholinesterase inhibitors: Synthesis, computational and pharmacological study",
volume = "101",
pages = "117649",
doi = "10.1016/j.bmc.2024.117649"
}

Jevtić, I. I., Suručić, R. V., Tovilović-Kovačević, G., Zogović, N., Kostić-Rajačić, S. V., Andrić, D.,& Penjišević, J. Z.. (2024). Multi-target potential of newly designed tacrine-derived cholinesterase inhibitors: Synthesis, computational and pharmacological study. in Bioorganic & Medicinal Chemistry
Elsevier., 101, 117649.
https://doi.org/10.1016/j.bmc.2024.117649

Jevtić II, Suručić RV, Tovilović-Kovačević G, Zogović N, Kostić-Rajačić SV, Andrić D, Penjišević JZ. Multi-target potential of newly designed tacrine-derived cholinesterase inhibitors: Synthesis, computational and pharmacological study. in Bioorganic & Medicinal Chemistry. 2024;101:117649.
doi:10.1016/j.bmc.2024.117649 .

Jevtić, Ivana I., Suručić, Relja V., Tovilović-Kovačević, Gordana, Zogović, Nevena, Kostić-Rajačić, Sladjana V., Andrić, Deana, Penjišević, Jelena Z., "Multi-target potential of newly designed tacrine-derived cholinesterase inhibitors: Synthesis, computational and pharmacological study" in Bioorganic & Medicinal Chemistry, 101 (2024):117649,
https://doi.org/10.1016/j.bmc.2024.117649 . .

TY  - CONF
AU  - Jevtić, Ivana I.
AU  - Andrić, Deana
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Dukić-Stefanović, Slađana
AU  - Kostić-Rajačić, Slađana
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5866
PB  - EFMC-YMCS
C3  - EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France
T1  - Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands
SP  - 66
EP  - 66
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5866
ER  - 

@conference{
author = "Jevtić, Ivana I. and Andrić, Deana and Penjišević, Jelena and Šukalović, Vladimir and Dukić-Stefanović, Slađana and Kostić-Rajačić, Slađana",
year = "2022",
publisher = "EFMC-YMCS",
journal = "EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France",
title = "Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands",
pages = "66-66",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5866"
}

Jevtić, I. I., Andrić, D., Penjišević, J., Šukalović, V., Dukić-Stefanović, S.,& Kostić-Rajačić, S.. (2022). Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands. in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France
EFMC-YMCS., 66-66.
https://hdl.handle.net/21.15107/rcub_cherry_5866

Jevtić II, Andrić D, Penjišević J, Šukalović V, Dukić-Stefanović S, Kostić-Rajačić S. Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands. in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France. 2022;:66-66.
https://hdl.handle.net/21.15107/rcub_cherry_5866 .

Jevtić, Ivana I., Andrić, Deana, Penjišević, Jelena, Šukalović, Vladimir, Dukić-Stefanović, Slađana, Kostić-Rajačić, Slađana, "Structure-activity relationship, docking analysis and ADME properties of newly designed, potent serotonin 5HT1a receptor ligands" in EFMC-YMCS Young Medicinal Chemists' Symposium, Nica, France (2022):66-66,
https://hdl.handle.net/21.15107/rcub_cherry_5866 .

TY  - JOUR
AU  - Dukić-Stefanović, Slađana
AU  - Hang Lai, Thu
AU  - Toussaint, Magali
AU  - Clauß, Oliver
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Ludwig, Friedrich-Alexander
AU  - Gündel, Daniel
AU  - Deuther-Conrad, Winnie
AU  - Kostić-Rajačić, Slađana
AU  - Brust, Peter
AU  - Teodoro, Rodrigo
PY  - 2021
UR  - https://www.sciencedirect.com/science/article/pii/S0960894X21004819
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4591
AB  - Monoamine oxidases (MAOs) play a key role in the metabolism of major monoamine neurotransmitters. In particular, the upregulation of MAO-B in Parkinson’s disease, Alzheimer’s disease and cancer augmented the development of selective MAO-B inhibitors for diagnostic and therapeutic purposes, such as the anti-parkinsonian MAO-B irreversible binder l-deprenyl (Selegiline®). Herein we report on the synthesis of novel fluorinated indanone derivatives for PET imaging of MAO-B in the brain. Out of our series, the derivatives 6, 8, 9 and 13 are amongst the most affine and selective ligands for MAO-B reported so far. For the derivative 6-((3-fluorobenzyl)oxy)-2,3-dihydro-1H-inden-1-one (6) exhibiting an outstanding affinity (Ki MAO-B = 6 nM), an automated copper-mediated radiofluorination starting from the pinacol boronic ester 17 is described. An in vitro screening in different species revealed a MAO-B region-specific accumulation of [18F]6 in rats and piglets in comparison to L-[3H]deprenyl. The pre-clinical in vivo assessment of [18F]6 in mice demonstrated the potential of indanones to readily cross the blood–brain barrier. Nonetheless, parallel in vivo metabolism studies indicated the presence of blood–brain barrier metabolites, thus arguing for further structural modifications. With the matching analytical profiles of the radiometabolite analysis from the in vitro liver microsome studies and the in vivo evaluation, the structure’s elucidation of the blood–brain barrier penetrant radiometabolites is possible and will serve as basis for the development of new indanone derivatives suitable for the PET imaging of MAO-B.
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain
VL  - 48
SP  - 128254
DO  - 10.1016/j.bmcl.2021.128254
ER  - 

@article{
author = "Dukić-Stefanović, Slađana and Hang Lai, Thu and Toussaint, Magali and Clauß, Oliver and Jevtić, Ivana I. and Penjišević, Jelena and Andrić, Deana and Ludwig, Friedrich-Alexander and Gündel, Daniel and Deuther-Conrad, Winnie and Kostić-Rajačić, Slađana and Brust, Peter and Teodoro, Rodrigo",
year = "2021",
abstract = "Monoamine oxidases (MAOs) play a key role in the metabolism of major monoamine neurotransmitters. In particular, the upregulation of MAO-B in Parkinson’s disease, Alzheimer’s disease and cancer augmented the development of selective MAO-B inhibitors for diagnostic and therapeutic purposes, such as the anti-parkinsonian MAO-B irreversible binder l-deprenyl (Selegiline®). Herein we report on the synthesis of novel fluorinated indanone derivatives for PET imaging of MAO-B in the brain. Out of our series, the derivatives 6, 8, 9 and 13 are amongst the most affine and selective ligands for MAO-B reported so far. For the derivative 6-((3-fluorobenzyl)oxy)-2,3-dihydro-1H-inden-1-one (6) exhibiting an outstanding affinity (Ki MAO-B = 6 nM), an automated copper-mediated radiofluorination starting from the pinacol boronic ester 17 is described. An in vitro screening in different species revealed a MAO-B region-specific accumulation of [18F]6 in rats and piglets in comparison to L-[3H]deprenyl. The pre-clinical in vivo assessment of [18F]6 in mice demonstrated the potential of indanones to readily cross the blood–brain barrier. Nonetheless, parallel in vivo metabolism studies indicated the presence of blood–brain barrier metabolites, thus arguing for further structural modifications. With the matching analytical profiles of the radiometabolite analysis from the in vitro liver microsome studies and the in vivo evaluation, the structure’s elucidation of the blood–brain barrier penetrant radiometabolites is possible and will serve as basis for the development of new indanone derivatives suitable for the PET imaging of MAO-B.",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain",
volume = "48",
pages = "128254",
doi = "10.1016/j.bmcl.2021.128254"
}

Dukić-Stefanović, S., Hang Lai, T., Toussaint, M., Clauß, O., Jevtić, I. I., Penjišević, J., Andrić, D., Ludwig, F., Gündel, D., Deuther-Conrad, W., Kostić-Rajačić, S., Brust, P.,& Teodoro, R.. (2021). In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain. in Bioorganic & Medicinal Chemistry Letters
Elsevier., 48, 128254.
https://doi.org/10.1016/j.bmcl.2021.128254

Dukić-Stefanović S, Hang Lai T, Toussaint M, Clauß O, Jevtić II, Penjišević J, Andrić D, Ludwig F, Gündel D, Deuther-Conrad W, Kostić-Rajačić S, Brust P, Teodoro R. In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain. in Bioorganic & Medicinal Chemistry Letters. 2021;48:128254.
doi:10.1016/j.bmcl.2021.128254 .

Dukić-Stefanović, Slađana, Hang Lai, Thu, Toussaint, Magali, Clauß, Oliver, Jevtić, Ivana I., Penjišević, Jelena, Andrić, Deana, Ludwig, Friedrich-Alexander, Gündel, Daniel, Deuther-Conrad, Winnie, Kostić-Rajačić, Slađana, Brust, Peter, Teodoro, Rodrigo, "In vitro and in vivo evaluation of fluorinated indanone derivatives as potential positron emission tomography agents for the imaging of monoamine oxidase B in the brain" in Bioorganic & Medicinal Chemistry Letters, 48 (2021):128254,
https://doi.org/10.1016/j.bmcl.2021.128254 . .

TY  - DATA
AU  - Dukić-Stefanović, Slađana
AU  - Hang Lai, Thu
AU  - Toussaint, Magali
AU  - Clauß, Oliver
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Ludwig, Friedrich-Alexander
AU  - Gündel, Daniel
AU  - Deuther-Conrad, Winnie
AU  - Kostić-Rajačić, Slađana
AU  - Brust, Peter
AU  - Teodoro, Rodrigo
PY  - 2021
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4592
PB  - Elsevier
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4592
ER  - 

@misc{
author = "Dukić-Stefanović, Slađana and Hang Lai, Thu and Toussaint, Magali and Clauß, Oliver and Jevtić, Ivana I. and Penjišević, Jelena and Andrić, Deana and Ludwig, Friedrich-Alexander and Gündel, Daniel and Deuther-Conrad, Winnie and Kostić-Rajačić, Slađana and Brust, Peter and Teodoro, Rodrigo",
year = "2021",
publisher = "Elsevier",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4592"
}

Dukić-Stefanović, S., Hang Lai, T., Toussaint, M., Clauß, O., Jevtić, I. I., Penjišević, J., Andrić, D., Ludwig, F., Gündel, D., Deuther-Conrad, W., Kostić-Rajačić, S., Brust, P.,& Teodoro, R.. (2021). Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.. in Bioorganic & Medicinal Chemistry Letters
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_4592

Dukić-Stefanović S, Hang Lai T, Toussaint M, Clauß O, Jevtić II, Penjišević J, Andrić D, Ludwig F, Gündel D, Deuther-Conrad W, Kostić-Rajačić S, Brust P, Teodoro R. Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254.. in Bioorganic & Medicinal Chemistry Letters. 2021;.
https://hdl.handle.net/21.15107/rcub_cherry_4592 .

Dukić-Stefanović, Slađana, Hang Lai, Thu, Toussaint, Magali, Clauß, Oliver, Jevtić, Ivana I., Penjišević, Jelena, Andrić, Deana, Ludwig, Friedrich-Alexander, Gündel, Daniel, Deuther-Conrad, Winnie, Kostić-Rajačić, Slađana, Brust, Peter, Teodoro, Rodrigo, "Supplementary data for the article: Dukić-Stefanović, S.; Hang Lai, T.; Toussaint, M.; Clauß, O.; Jevtić, I. I.; Penjišević, J. Z.; Andrić, D.; Ludwig, F.-A.; Gündel, D.; Deuther-Conrad, W.; Kostić-Rajačić, S. V.; Brust, P.; Teodoro, R. In Vitro and in Vivo Evaluation of Fluorinated Indanone Derivatives as Potential Positron Emission Tomography Agents for the Imaging of Monoamine Oxidase B in the Brain. Bioorganic & Medicinal Chemistry Letters 2021, 48, 128254. https://doi.org/10.1016/j.bmcl.2021.128254." in Bioorganic & Medicinal Chemistry Letters (2021),
https://hdl.handle.net/21.15107/rcub_cherry_4592 .

TY  - CONF
AU  - Andrić, Deana
AU  - Dukić-Stefanović, Sladjana
AU  - Penjišević, Jelena 
AU  - Jevtić, Ivana I.
AU  - Šukalović, Vladimir 
AU  - Suručić, Relja
AU  - Kostić-Rajačić, Sladjana V.
PY  - 2021
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5282
AB  - 5HT1A receptor targeting drugs have been used as the treatment for the many neuropsychiatric
disorders, such as schizophrenia and depression. As a part of ongoing research, we designed series of
new compounds that share arylpiperazine common structural motif with the 5HT1A receptor ligand
aripiprazole. Receptor-ligand interactions were determined by the molecular docking simulations,
revealing the positive impact of the phenyl substitution in the arylpiperazine part of the molecules. Nine
selected compounds were synthesized in four reaction steps in high overall yields (59-73%). In vitro
pharmacological evaluation of the synthesized compounds revealed three compounds (5b, 6b and 6c)
with high 5HT1A binding affinity, comparable with aripiprazole (Ki 12.0, 4.8, 12.8, 5.6 nM,
respectively). Compounds from b series, 5b and 6b, possess 2-methoxyphenyl substituents, while 6c
possess 2,3-dichlorophenyl substituent in the arylpiperazine part of the molecule. The pharmacological
results are therefore in accordance with the molecular docking simulations thus proving the rational
design. Compounds 5c, 6b and 6c can be considered as the candidates for further evaluation as new,
potential antidepressants.
C3  - 1st International Conference on Chemo and BioInformatics (ICCBIKG 2021), Kragujevac, Serbia, 26-27th October 2021
T1  - Design, synthesis and pharmacological evaluation of N-{4-[2-(4-aryl-piperazin-1-yl)-ethyl]-phenyl}-arylamides
DO  - 10.46793/ICCBI21.355A
ER  - 

@conference{
author = "Andrić, Deana and Dukić-Stefanović, Sladjana and Penjišević, Jelena  and Jevtić, Ivana I. and Šukalović, Vladimir  and Suručić, Relja and Kostić-Rajačić, Sladjana V.",
year = "2021",
abstract = "5HT1A receptor targeting drugs have been used as the treatment for the many neuropsychiatric
disorders, such as schizophrenia and depression. As a part of ongoing research, we designed series of
new compounds that share arylpiperazine common structural motif with the 5HT1A receptor ligand
aripiprazole. Receptor-ligand interactions were determined by the molecular docking simulations,
revealing the positive impact of the phenyl substitution in the arylpiperazine part of the molecules. Nine
selected compounds were synthesized in four reaction steps in high overall yields (59-73%). In vitro
pharmacological evaluation of the synthesized compounds revealed three compounds (5b, 6b and 6c)
with high 5HT1A binding affinity, comparable with aripiprazole (Ki 12.0, 4.8, 12.8, 5.6 nM,
respectively). Compounds from b series, 5b and 6b, possess 2-methoxyphenyl substituents, while 6c
possess 2,3-dichlorophenyl substituent in the arylpiperazine part of the molecule. The pharmacological
results are therefore in accordance with the molecular docking simulations thus proving the rational
design. Compounds 5c, 6b and 6c can be considered as the candidates for further evaluation as new,
potential antidepressants.",
journal = "1st International Conference on Chemo and BioInformatics (ICCBIKG 2021), Kragujevac, Serbia, 26-27th October 2021",
title = "Design, synthesis and pharmacological evaluation of N-{4-[2-(4-aryl-piperazin-1-yl)-ethyl]-phenyl}-arylamides",
doi = "10.46793/ICCBI21.355A"
}

Andrić, D., Dukić-Stefanović, S., Penjišević, J., Jevtić, I. I., Šukalović, V., Suručić, R.,& Kostić-Rajačić, S. V.. (2021). Design, synthesis and pharmacological evaluation of N-{4-[2-(4-aryl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in 1st International Conference on Chemo and BioInformatics (ICCBIKG 2021), Kragujevac, Serbia, 26-27th October 2021.
https://doi.org/10.46793/ICCBI21.355A

Andrić D, Dukić-Stefanović S, Penjišević J, Jevtić II, Šukalović V, Suručić R, Kostić-Rajačić SV. Design, synthesis and pharmacological evaluation of N-{4-[2-(4-aryl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in 1st International Conference on Chemo and BioInformatics (ICCBIKG 2021), Kragujevac, Serbia, 26-27th October 2021. 2021;.
doi:10.46793/ICCBI21.355A .

Andrić, Deana, Dukić-Stefanović, Sladjana, Penjišević, Jelena , Jevtić, Ivana I., Šukalović, Vladimir , Suručić, Relja, Kostić-Rajačić, Sladjana V., "Design, synthesis and pharmacological evaluation of N-{4-[2-(4-aryl-piperazin-1-yl)-ethyl]-phenyl}-arylamides" in 1st International Conference on Chemo and BioInformatics (ICCBIKG 2021), Kragujevac, Serbia, 26-27th October 2021 (2021),
https://doi.org/10.46793/ICCBI21.355A . .

TY  - CONF
AU  - Teodoro, R.
AU  - Dukić-Stefanović, Sladjana
AU  - Lai, T. H.
AU  - Claus, O.
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena 
AU  - Toussaint, M.
AU  - Deuther-Conrad, W.
AU  - Gundel, D.
AU  - Andrić, Deana
AU  - Scheunemann, M.
AU  - Kostić-Rajačić, Sladjana V.
AU  - Burst, P.
PY  - 2020
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5284
AB  - Ziel/Aim The monoamine oxidase B (MAO B) isoenzyme is known to be
involved in the oxidative deamination of biogenic amines. While the use of
MAO B inhibitors is already well-established for the treatment of Parkinson’s
disease, recent reports suggest its involvement in certain types of brain
tumors.1 We herein aim at the synthesis and preclinical evaluation of fluorinated indanone-based derivatives targeting MAO B in the brain via positron
emission tomography (PET).
Methodik/Methods A small series of fluorinated indanone derivatives
was obtained via the O-alkylation or esterification starting with the
commercially available 6-hydroxy-2,3-dihydro-1H-inden-1-one in one or
two steps. Binding affinities towards the human MAO isoenzymes were
estimated in vitro by radioligand displacement. HL126 was selected for
radiofluorination via its corresponding boronic acid pinacol ester. In
vitro autoradiography of [18F]HL126 was performed in mice brain slices.
In vivo evaluation of [18F]HL126 in CD-1 mice was carried out and
metabolism studies were performed in plasma and brain samples via
radio-HPLC.
Ergebnisse/Results The fluorinated indanone derivatives were synthesized
in yields ranging from 65-89 %. The fluorophenyl ether derivative, HL126,
was further selected for radiofluorination based on its high binding affinity
towards MAO B (Ki = 6.9 ± 5.3 nM). [18F]HL126 was obtained by an alcohol-enhanced copper-mediated approach via the corresponding boronic
acid pinacol ester precursor with radiochemical yields of about 11 ± 3 %,
high radiochemical purities (≥99 %) and molar activities in the range of 20
GBq/mmol. In vitro autoradiography showed a specific blockade with
selective MAO-A/B inhibitors. PET/MRI analyses revealed that [18F]HL126
readily enters the brain. Some radiometabolites do cross the blood-brain
barrier.
Schlussfolgerungen/Conclusions Although metabolism studies with [18F]
HL126 revealed the presence of radiometabolites in the brain, the high binding affinity towards MAO B and the pronounced selectivity in in vitro autoradiography studies encourage further derivatization of indanone-based
scaffolds for targeting MAO B.
C3  - 58th Annual Meeting of the German Society for Nuclear Medicine,  Leipzig, Germany
T1  - Development of fluorinated indanone-based derivatives for the imaging of monoamine oxidase B via positron emission tomography
VL  - 59
DO  - 10.1055/s-0040-1708201
ER  - 

@conference{
author = "Teodoro, R. and Dukić-Stefanović, Sladjana and Lai, T. H. and Claus, O. and Jevtić, Ivana I. and Penjišević, Jelena  and Toussaint, M. and Deuther-Conrad, W. and Gundel, D. and Andrić, Deana and Scheunemann, M. and Kostić-Rajačić, Sladjana V. and Burst, P.",
year = "2020",
abstract = "Ziel/Aim The monoamine oxidase B (MAO B) isoenzyme is known to be
involved in the oxidative deamination of biogenic amines. While the use of
MAO B inhibitors is already well-established for the treatment of Parkinson’s
disease, recent reports suggest its involvement in certain types of brain
tumors.1 We herein aim at the synthesis and preclinical evaluation of fluorinated indanone-based derivatives targeting MAO B in the brain via positron
emission tomography (PET).
Methodik/Methods A small series of fluorinated indanone derivatives
was obtained via the O-alkylation or esterification starting with the
commercially available 6-hydroxy-2,3-dihydro-1H-inden-1-one in one or
two steps. Binding affinities towards the human MAO isoenzymes were
estimated in vitro by radioligand displacement. HL126 was selected for
radiofluorination via its corresponding boronic acid pinacol ester. In
vitro autoradiography of [18F]HL126 was performed in mice brain slices.
In vivo evaluation of [18F]HL126 in CD-1 mice was carried out and
metabolism studies were performed in plasma and brain samples via
radio-HPLC.
Ergebnisse/Results The fluorinated indanone derivatives were synthesized
in yields ranging from 65-89 %. The fluorophenyl ether derivative, HL126,
was further selected for radiofluorination based on its high binding affinity
towards MAO B (Ki = 6.9 ± 5.3 nM). [18F]HL126 was obtained by an alcohol-enhanced copper-mediated approach via the corresponding boronic
acid pinacol ester precursor with radiochemical yields of about 11 ± 3 %,
high radiochemical purities (≥99 %) and molar activities in the range of 20
GBq/mmol. In vitro autoradiography showed a specific blockade with
selective MAO-A/B inhibitors. PET/MRI analyses revealed that [18F]HL126
readily enters the brain. Some radiometabolites do cross the blood-brain
barrier.
Schlussfolgerungen/Conclusions Although metabolism studies with [18F]
HL126 revealed the presence of radiometabolites in the brain, the high binding affinity towards MAO B and the pronounced selectivity in in vitro autoradiography studies encourage further derivatization of indanone-based
scaffolds for targeting MAO B.",
journal = "58th Annual Meeting of the German Society for Nuclear Medicine,  Leipzig, Germany",
title = "Development of fluorinated indanone-based derivatives for the imaging of monoamine oxidase B via positron emission tomography",
volume = "59",
doi = "10.1055/s-0040-1708201"
}

Teodoro, R., Dukić-Stefanović, S., Lai, T. H., Claus, O., Jevtić, I. I., Penjišević, J., Toussaint, M., Deuther-Conrad, W., Gundel, D., Andrić, D., Scheunemann, M., Kostić-Rajačić, S. V.,& Burst, P.. (2020). Development of fluorinated indanone-based derivatives for the imaging of monoamine oxidase B via positron emission tomography. in 58th Annual Meeting of the German Society for Nuclear Medicine,  Leipzig, Germany, 59.
https://doi.org/10.1055/s-0040-1708201

Teodoro R, Dukić-Stefanović S, Lai TH, Claus O, Jevtić II, Penjišević J, Toussaint M, Deuther-Conrad W, Gundel D, Andrić D, Scheunemann M, Kostić-Rajačić SV, Burst P. Development of fluorinated indanone-based derivatives for the imaging of monoamine oxidase B via positron emission tomography. in 58th Annual Meeting of the German Society for Nuclear Medicine,  Leipzig, Germany. 2020;59.
doi:10.1055/s-0040-1708201 .

Teodoro, R., Dukić-Stefanović, Sladjana, Lai, T. H., Claus, O., Jevtić, Ivana I., Penjišević, Jelena , Toussaint, M., Deuther-Conrad, W., Gundel, D., Andrić, Deana, Scheunemann, M., Kostić-Rajačić, Sladjana V., Burst, P., "Development of fluorinated indanone-based derivatives for the imaging of monoamine oxidase B via positron emission tomography" in 58th Annual Meeting of the German Society for Nuclear Medicine,  Leipzig, Germany, 59 (2020),
https://doi.org/10.1055/s-0040-1708201 . .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Penjišević, Jelena
AU  - Savić-Vujović, Katarina
AU  - Srebro, Dragana
AU  - Vučković, Sonja M.
AU  - Ivanović, Milovan
AU  - Kostić-Rajačić, Slađana
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4243
AB  - Herein, the synthesis and pharmacological evaluation of 13 novel compounds, designed as potential heterobivalent ligands for μ-opioid receptor (MOR) and dopamine D2 receptors (D2DAR), are reported. The compounds consisted of anilido piperidine and N-aryl piperazine moieties, joined by a variable-length methylene linker. The two moieties represent MOR and D2DAR pharmacophores, respectively. The synthesis encompassed four steps, securing the final products in 28–42 % overall yields. The approach has a considerable synthetic potential, providing access to various related structures. Pharmacological tests involved in vitro competitive assay for D2DAR using [3H] spiperon, as a standard radioligand, and in vivo antinociceptive tests for MOR. The measured dopamine affinities were modest to low, while antinociceptive activity was completely absent. Therefore, the compounds of the general structure prepared in this research are unlikely to be useful as opioid–dopamine receptor heterobivalent ligands.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - μ-opioid/D2 dopamine receptor pharmacophore containing ligands: Synthesis and pharmacological evaluation
VL  - 85
IS  - 6
SP  - 711
EP  - 720
DO  - 10.2298/JSC190912118J
ER  - 

@article{
author = "Jevtić, Ivana I. and Penjišević, Jelena and Savić-Vujović, Katarina and Srebro, Dragana and Vučković, Sonja M. and Ivanović, Milovan and Kostić-Rajačić, Slađana",
year = "2020",
abstract = "Herein, the synthesis and pharmacological evaluation of 13 novel compounds, designed as potential heterobivalent ligands for μ-opioid receptor (MOR) and dopamine D2 receptors (D2DAR), are reported. The compounds consisted of anilido piperidine and N-aryl piperazine moieties, joined by a variable-length methylene linker. The two moieties represent MOR and D2DAR pharmacophores, respectively. The synthesis encompassed four steps, securing the final products in 28–42 % overall yields. The approach has a considerable synthetic potential, providing access to various related structures. Pharmacological tests involved in vitro competitive assay for D2DAR using [3H] spiperon, as a standard radioligand, and in vivo antinociceptive tests for MOR. The measured dopamine affinities were modest to low, while antinociceptive activity was completely absent. Therefore, the compounds of the general structure prepared in this research are unlikely to be useful as opioid–dopamine receptor heterobivalent ligands.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "μ-opioid/D2 dopamine receptor pharmacophore containing ligands: Synthesis and pharmacological evaluation",
volume = "85",
number = "6",
pages = "711-720",
doi = "10.2298/JSC190912118J"
}

Jevtić, I. I., Penjišević, J., Savić-Vujović, K., Srebro, D., Vučković, S. M., Ivanović, M.,& Kostić-Rajačić, S.. (2020). μ-opioid/D2 dopamine receptor pharmacophore containing ligands: Synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 85(6), 711-720.
https://doi.org/10.2298/JSC190912118J

Jevtić II, Penjišević J, Savić-Vujović K, Srebro D, Vučković SM, Ivanović M, Kostić-Rajačić S. μ-opioid/D2 dopamine receptor pharmacophore containing ligands: Synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society. 2020;85(6):711-720.
doi:10.2298/JSC190912118J .

Jevtić, Ivana I., Penjišević, Jelena, Savić-Vujović, Katarina, Srebro, Dragana, Vučković, Sonja M., Ivanović, Milovan, Kostić-Rajačić, Slađana, "μ-opioid/D2 dopamine receptor pharmacophore containing ligands: Synthesis and pharmacological evaluation" in Journal of the Serbian Chemical Society, 85, no. 6 (2020):711-720,
https://doi.org/10.2298/JSC190912118J . .

Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S.. (2019). Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier., 1124, 146-153.
https://doi.org/10.1016/j.jchromb.2019.06.006

Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;1124:146-153.
doi:10.1016/j.jchromb.2019.06.006 .

Šegan, Sandra B., Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić-Rajačić, Slađana, "Investigation of lipophilicity and pharmacokinetic properties of 2-(methoxy)phenylpiperazine dopamine D2 ligands" in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 1124 (2019):146-153,
https://doi.org/10.1016/j.jchromb.2019.06.006 . .

Šegan, S. B., Penjišević, J., Šukalović, V., Andrić, D., Milojković-Opsenica, D.,& Kostić-Rajačić, S.. (2019). Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences
Elsevier..
https://hdl.handle.net/21.15107/rcub_cherry_3697

Šegan SB, Penjišević J, Šukalović V, Andrić D, Milojković-Opsenica D, Kostić-Rajačić S. Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006. in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3697 .

Šegan, Sandra B., Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Milojković-Opsenica, Dušanka, Kostić-Rajačić, Slađana, "Supplementary data for the article: Šegan, S.; Penjišević, J.; Šukalović, V.; Andrić, D.; Milojković-Opsenica, D.; Kostić-Rajačić, S. Investigation of Lipophilicity and Pharmacokinetic Properties of 2-(Methoxy)Phenylpiperazine Dopamine D2 Ligands. Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences 2019, 1124, 146–153. https://doi.org/10.1016/j.jchromb.2019.06.006" in Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3697 .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Šukalović, Vladimir
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3661
AB  - A total of 14 novel arylpiperazines were synthesized, and pharmaco-logically evaluated by measuring their affinities towards the D2 dopamine receptor (DRD2) in a [3H]spiperone competition assay. All the herein described compounds consist of a benzimidazole moiety connected to N-(2-methoxyphenyl)piperazine via linkers of various lengths. Molecular docking analysis and molecular dynamics simulations were performed on the DRD2–arylpiperazine complexes with the objective of exploring the receptor–ligand interactions and properties of the receptor binding site. The recently published crystal structure of DRD2 was used throughout this study. The major finding is that high affinity arylpiperazines must interact with both the orthosteric binding site and the extended binding pocket of DRD2 and therefore should contain a linker of 5 or 6 methylene groups long.
PB  - Beograd : Srpsko hemijsko društvo
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor
VL  - 84
IS  - 9
SP  - 925
EP  - 934
DO  - 10.2298/JSC181029104P
ER  - 

@article{
author = "Penjišević, Jelena and Andrić, Deana and Šukalović, Vladimir and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2019",
abstract = "A total of 14 novel arylpiperazines were synthesized, and pharmaco-logically evaluated by measuring their affinities towards the D2 dopamine receptor (DRD2) in a [3H]spiperone competition assay. All the herein described compounds consist of a benzimidazole moiety connected to N-(2-methoxyphenyl)piperazine via linkers of various lengths. Molecular docking analysis and molecular dynamics simulations were performed on the DRD2–arylpiperazine complexes with the objective of exploring the receptor–ligand interactions and properties of the receptor binding site. The recently published crystal structure of DRD2 was used throughout this study. The major finding is that high affinity arylpiperazines must interact with both the orthosteric binding site and the extended binding pocket of DRD2 and therefore should contain a linker of 5 or 6 methylene groups long.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor",
volume = "84",
number = "9",
pages = "925-934",
doi = "10.2298/JSC181029104P"
}

Penjišević, J., Andrić, D., Šukalović, V., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2019). Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor. in Journal of the Serbian Chemical Society
Beograd : Srpsko hemijsko društvo., 84(9), 925-934.
https://doi.org/10.2298/JSC181029104P

Penjišević J, Andrić D, Šukalović V, Roglić G, Šoškić V, Kostić-Rajačić S. Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor. in Journal of the Serbian Chemical Society. 2019;84(9):925-934.
doi:10.2298/JSC181029104P .

Penjišević, Jelena, Andrić, Deana, Šukalović, Vladimir, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis of novel 2-(piperazino-1-yl-alkyl)-1H-benzimidazole derivates and assessment of their interactions with the D2 dopamine receptor" in Journal of the Serbian Chemical Society, 84, no. 9 (2019):925-934,
https://doi.org/10.2298/JSC181029104P . .

TY  - CONF
AU  - Penjišević, Jelena 
AU  - Andrić, Deana
AU  - Dukić-Stefanović, Sladjana
AU  - Spalholz, T.
AU  - Burst, P.
AU  - Kostić-Rajačić, Sladjana V.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5283
AB  - Serotonin 5HT1a receptor belongs to a class of G-protein coupled receptors. It serves as a
potential target for neurological disorders such as depression, anxiety etc. It is a well-known
fact that N-arylpiperazine moiety is present in compounds with pronounced 5HT1a activity.
Taking into account previously published results1
novel structures of N-{4-[2-(4-
arylpiperazin-1-yl)ethyl]phenyl}arylamides (Figure 1.) were designed for target synthesis.
Proposed modifications include: different position of hydroxyl group in aryl amide part of
molecule and addition of methoxy and chloro substituents to the phenyl ring of parent
compounds, since their introduction in the molecule leads to increased receptor affinity.
New compounds were synthesized by acylation of N-arylpiperazines using 4-
nitrophenylacetic acid. Obtained amides were converted in 1-(4-nitrophenethyl)-4-
arylpiperazines using diborane in THF. Reduction of nitro compounds by Ra/Ni provided 1-
(4-aminophenethyl)-4-arylpiperazines. Target arylamides were obtained by condensation 1-
(4-aminophenethyl)-4-arylpiperazines with corresponding aryl acids in presence of
propylphosphoric acid anhydride (PPAA) in DMF.
All newly synthesized compounds were evaluated for their activity toward 5HT1a receptors
by in vitro competitive displacement assay of [3H] 8-OH-DPAT. HEK cell line were used as a
source of 5HT1a receptors.
Introduction of 2-methoxy and 2,3-dichloro groups,as well as meta and para hydroxyl group
in molecule resulted in increment of affinity toward 5HT1a receptors comparing to the parent
compounds.
C3  - 11th Joint Meeting on Medicinal Chemistry 2019, Prague, Czech Republic, 2019.
T1  - Synthesis and pharmacological evaluation of N-{4-[2-(4-arylpiperazin-1-yl) ethyl] phenyl}arylamides
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5283
ER  - 

@conference{
author = "Penjišević, Jelena  and Andrić, Deana and Dukić-Stefanović, Sladjana and Spalholz, T. and Burst, P. and Kostić-Rajačić, Sladjana V.",
year = "2019",
abstract = "Serotonin 5HT1a receptor belongs to a class of G-protein coupled receptors. It serves as a
potential target for neurological disorders such as depression, anxiety etc. It is a well-known
fact that N-arylpiperazine moiety is present in compounds with pronounced 5HT1a activity.
Taking into account previously published results1
novel structures of N-{4-[2-(4-
arylpiperazin-1-yl)ethyl]phenyl}arylamides (Figure 1.) were designed for target synthesis.
Proposed modifications include: different position of hydroxyl group in aryl amide part of
molecule and addition of methoxy and chloro substituents to the phenyl ring of parent
compounds, since their introduction in the molecule leads to increased receptor affinity.
New compounds were synthesized by acylation of N-arylpiperazines using 4-
nitrophenylacetic acid. Obtained amides were converted in 1-(4-nitrophenethyl)-4-
arylpiperazines using diborane in THF. Reduction of nitro compounds by Ra/Ni provided 1-
(4-aminophenethyl)-4-arylpiperazines. Target arylamides were obtained by condensation 1-
(4-aminophenethyl)-4-arylpiperazines with corresponding aryl acids in presence of
propylphosphoric acid anhydride (PPAA) in DMF.
All newly synthesized compounds were evaluated for their activity toward 5HT1a receptors
by in vitro competitive displacement assay of [3H] 8-OH-DPAT. HEK cell line were used as a
source of 5HT1a receptors.
Introduction of 2-methoxy and 2,3-dichloro groups,as well as meta and para hydroxyl group
in molecule resulted in increment of affinity toward 5HT1a receptors comparing to the parent
compounds.",
journal = "11th Joint Meeting on Medicinal Chemistry 2019, Prague, Czech Republic, 2019.",
title = "Synthesis and pharmacological evaluation of N-{4-[2-(4-arylpiperazin-1-yl) ethyl] phenyl}arylamides",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5283"
}

Penjišević, J., Andrić, D., Dukić-Stefanović, S., Spalholz, T., Burst, P.,& Kostić-Rajačić, S. V.. (2019). Synthesis and pharmacological evaluation of N-{4-[2-(4-arylpiperazin-1-yl) ethyl] phenyl}arylamides. in 11th Joint Meeting on Medicinal Chemistry 2019, Prague, Czech Republic, 2019..
https://hdl.handle.net/21.15107/rcub_cherry_5283

Penjišević J, Andrić D, Dukić-Stefanović S, Spalholz T, Burst P, Kostić-Rajačić SV. Synthesis and pharmacological evaluation of N-{4-[2-(4-arylpiperazin-1-yl) ethyl] phenyl}arylamides. in 11th Joint Meeting on Medicinal Chemistry 2019, Prague, Czech Republic, 2019.. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_5283 .

Penjišević, Jelena , Andrić, Deana, Dukić-Stefanović, Sladjana, Spalholz, T., Burst, P., Kostić-Rajačić, Sladjana V., "Synthesis and pharmacological evaluation of N-{4-[2-(4-arylpiperazin-1-yl) ethyl] phenyl}arylamides" in 11th Joint Meeting on Medicinal Chemistry 2019, Prague, Czech Republic, 2019. (2019),
https://hdl.handle.net/21.15107/rcub_cherry_5283 .

TY  - JOUR
AU  - Kostić-Rajačić, Slađana
AU  - Schwall, Gerhard
AU  - Penjišević, Jelena
AU  - Andrić, Deana
AU  - Šukalović, Vladimir
AU  - Šoškić, Vukić
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2167
AB  - Affinity chromatography was used to identify potential cellular targets that are responsible for neuroprotective activity of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. Active and inactive representatives of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides bearing an extended linker were synthesized and immobilized on an agarose-based matrix. This was followed by the identification of specifically bound proteins isolated out of the whole rat brain extract. Inducible flavoprotein NAD(P)H:quinone oxidoreductase (NQO1) was identified as candidates for cellular targets.
PB  - Wiley, Hoboken
T2  - Chemical Biology and Drug Design
T1  - Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides
VL  - 92
IS  - 1
SP  - 1393
EP  - 1397
DO  - 10.1111/cbdd.13193
ER  - 

@article{
author = "Kostić-Rajačić, Slađana and Schwall, Gerhard and Penjišević, Jelena and Andrić, Deana and Šukalović, Vladimir and Šoškić, Vukić",
year = "2018",
abstract = "Affinity chromatography was used to identify potential cellular targets that are responsible for neuroprotective activity of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. Active and inactive representatives of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides bearing an extended linker were synthesized and immobilized on an agarose-based matrix. This was followed by the identification of specifically bound proteins isolated out of the whole rat brain extract. Inducible flavoprotein NAD(P)H:quinone oxidoreductase (NQO1) was identified as candidates for cellular targets.",
publisher = "Wiley, Hoboken",
journal = "Chemical Biology and Drug Design",
title = "Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides",
volume = "92",
number = "1",
pages = "1393-1397",
doi = "10.1111/cbdd.13193"
}

Kostić-Rajačić, S., Schwall, G., Penjišević, J., Andrić, D., Šukalović, V.,& Šoškić, V.. (2018). Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in Chemical Biology and Drug Design
Wiley, Hoboken., 92(1), 1393-1397.
https://doi.org/10.1111/cbdd.13193

Kostić-Rajačić S, Schwall G, Penjišević J, Andrić D, Šukalović V, Šoškić V. Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides. in Chemical Biology and Drug Design. 2018;92(1):1393-1397.
doi:10.1111/cbdd.13193 .

Kostić-Rajačić, Slađana, Schwall, Gerhard, Penjišević, Jelena, Andrić, Deana, Šukalović, Vladimir, Šoškić, Vukić, "Identification of NQO1 and ferrochelatase as interaction partners for neuroprotective N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides" in Chemical Biology and Drug Design, 92, no. 1 (2018):1393-1397,
https://doi.org/10.1111/cbdd.13193 . .

TY  - JOUR
AU  - Popović-Đorđevic, Jelena
AU  - Jevtić, Ivana I.
AU  - Grozdanic, Nadja Dj
AU  - Šegan, Sandra B.
AU  - Zlatović, Mario
AU  - Ivanović, Milovan
AU  - Stanojković, Tatjana
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2383
AB  - The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.
PB  - Taylor & Francis Ltd, Abingdon
T2  - Journal of Enzyme Inhibition and Medicinal Chemistry
T1  - alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives
VL  - 32
IS  - 1
SP  - 298
EP  - 303
DO  - 10.1080/14756366.2016.1250754
ER  - 

@article{
author = "Popović-Đorđevic, Jelena and Jevtić, Ivana I. and Grozdanic, Nadja Dj and Šegan, Sandra B. and Zlatović, Mario and Ivanović, Milovan and Stanojković, Tatjana",
year = "2017",
abstract = "The inhibitory activities of selected cyclic urea and carbamate derivatives (1-13) toward alpha-glucosidase (alpha-Gls) in in vitro assay were examined in this study. All examined compounds showed higher inhibitory activity (IC50) against alpha-Gls compared to standard antidiabetic drug acarbose. The most potent was benzyl (3,4,5-trimethoxyphenyl) carbamate (12) with IC50 = 49.85 +/- 0.10 mu M. In vitro cytotoxicity of the investigated compounds was tested on three human cancer cell lines HeLa, A549 and MDA-MB-453 using MTT assay. The best antitumour activity was achieved with compound 2 (trans-5-phenethyl-1-phenylhexahydro-1H-imidazo[4,5-c] pyridin-2(3H)-one) against MDA-MB-453 human breast cancer cell line (IC50 = 83.41 +/- 1.60 mu M). Cyclic ureas and carbamates showed promising anti-alpha-glucosidase activity and should be further tested as potential antidiabetic drugs. The PLS model of preliminary QSAR study indicated that, in planing the future synthesis of more potent compounds, the newly designed should have the substituents capable of polar interactions with receptor sites in various positions, while avoiding the increase of their lipophilicity.",
publisher = "Taylor & Francis Ltd, Abingdon",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
title = "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives",
volume = "32",
number = "1",
pages = "298-303",
doi = "10.1080/14756366.2016.1250754"
}

Popović-Đorđevic, J., Jevtić, I. I., Grozdanic, N. D., Šegan, S. B., Zlatović, M., Ivanović, M.,& Stanojković, T.. (2017). alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry
Taylor & Francis Ltd, Abingdon., 32(1), 298-303.
https://doi.org/10.1080/14756366.2016.1250754

Popović-Đorđevic J, Jevtić II, Grozdanic ND, Šegan SB, Zlatović M, Ivanović M, Stanojković T. alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives. in Journal of Enzyme Inhibition and Medicinal Chemistry. 2017;32(1):298-303.
doi:10.1080/14756366.2016.1250754 .

Popović-Đorđevic, Jelena, Jevtić, Ivana I., Grozdanic, Nadja Dj, Šegan, Sandra B., Zlatović, Mario, Ivanović, Milovan, Stanojković, Tatjana, "alpha-Glucosidase inhibitory activity and cytotoxic effects of some cyclic urea and carbamate derivatives" in Journal of Enzyme Inhibition and Medicinal Chemistry, 32, no. 1 (2017):298-303,
https://doi.org/10.1080/14756366.2016.1250754 . .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Todorović, Nina
AU  - Ivanović, Milovan
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2492
AB  - The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl
VL  - 49
IS  - 14
SP  - 3126
EP  - 3136
DO  - 10.1055/s-0036-1588985
ER  - 

@article{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Todorović, Nina and Ivanović, Milovan",
year = "2017",
abstract = "The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl",
volume = "49",
number = "14",
pages = "3126-3136",
doi = "10.1055/s-0036-1588985"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R., Todorović, N.,& Ivanović, M.. (2017). Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl. in Synthesis, Stuttgart
Georg Thieme Verlag Kg, Stuttgart., 49(14), 3126-3136.
https://doi.org/10.1055/s-0036-1588985

Jevtić II, Došen-Mićović L, Ivanović ER, Todorović N, Ivanović M. Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl. in Synthesis, Stuttgart. 2017;49(14):3126-3136.
doi:10.1055/s-0036-1588985 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Todorović, Nina, Ivanović, Milovan, "Synthesis of Orthogonally Protected (+/-)-3-Amino-4-anilidopiperidines and (+/-)-3-N-Carbomethoxyfentanyl" in Synthesis, Stuttgart, 49, no. 14 (2017):3126-3136,
https://doi.org/10.1055/s-0036-1588985 . .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Todorović, Nina
AU  - Ivanović, Milovan
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3248
AB  - The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl
VL  - 49
IS  - 14
SP  - 3126
EP  - 3136
DO  - 10.1055/s-0036-1588985
ER  - 

@article{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Todorović, Nina and Ivanović, Milovan",
year = "2017",
abstract = "The synthesis of orthogonally protected cis- and trans-3-amino-4-anilidopiperidine derivatives has been accomplished in six steps, starting from readily accessible 4-piperidone derivatives. The last three steps, i.e., N-acylation, Hofmann rearrangement, and carbamate cleavage, involved separated (+/-)-cis and (+/-)-trans intermediates. Complete retention of configuration was observed at position 3 of the piperidine ring. Specifically protected positions 1 and 3 at the piperidine scaffold allow for selective deprotection and introduction of diverse substituents at the respective nitrogen sites. The orthogonally protected anilidopiperidines open avenues to potentially pharmacologically active compounds, including opioids and various bivalent ligands for G protein-coupled receptors. In addition, a prototype of a novel class of fentanyl derivatives, possessing a 3-amino group, was synthesized by using the same approach.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl",
volume = "49",
number = "14",
pages = "3126-3136",
doi = "10.1055/s-0036-1588985"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R., Todorović, N.,& Ivanović, M.. (2017). Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. in Synthesis
Georg Thieme Verlag Kg, Stuttgart., 49(14), 3126-3136.
https://doi.org/10.1055/s-0036-1588985

Jevtić II, Došen-Mićović L, Ivanović ER, Todorović N, Ivanović M. Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. in Synthesis. 2017;49(14):3126-3136.
doi:10.1055/s-0036-1588985 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Todorović, Nina, Ivanović, Milovan, "Synthesis of Orthogonally Protected (±)-3-Amino-4-anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl" in Synthesis, 49, no. 14 (2017):3126-3136,
https://doi.org/10.1055/s-0036-1588985 . .

TY  - DATA
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Todorović, Nina
AU  - Ivanović, Milovan
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3249
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis
T1  - Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3249
ER  - 

@misc{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Todorović, Nina and Ivanović, Milovan",
year = "2017",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis",
title = "Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3249"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R., Todorović, N.,& Ivanović, M.. (2017). Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985. in Synthesis
Georg Thieme Verlag Kg, Stuttgart..
https://hdl.handle.net/21.15107/rcub_cherry_3249

Jevtić II, Došen-Mićović L, Ivanović ER, Todorović N, Ivanović M. Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985. in Synthesis. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3249 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Todorović, Nina, Ivanović, Milovan, "Supplementary material for the article: Jevtić, I. I.; Došen-Mićović, L. I.; Ivanović, E. R.; Todorović, N. M.; Ivanović, M. D. Synthesis of Orthogonally Protected (±)-3-Amino-4-Anilidopiperidines and (±)-3- N -Carbomethoxyfentanyl. Synthesis (Germany) 2017, 49 (14), 3126–3136. https://doi.org/10.1055/s-0036-1588985" in Synthesis (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3249 .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Novaković, Irena T.
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1937
AB  - A series of sixteen novel substituted piperidines and (2-methoxyphenyl)piperazines were synthesized, starting from the key intermediates 1-(2-methoxyphenyl)-4-(piperidin-4-yl)piperazine and 1-(2-methoxyphenyl)-4-[(piperidin-4-yl)methyl] piperazine. Biological evaluation of the synthesized compounds was illustrated by seven compounds, of which 1-(2-methoxyphenyl)-4-{[1-(2-nitrobenzyl) piperidin-4-yl] methyl} piperazine had the highest affinity for the dopamine D-2 receptor. For all seven selected compounds, docking analysis was performed in order to establish their structure-to-activity relationship.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines
VL  - 81
IS  - 4
SP  - 347
EP  - 356
DO  - 10.2298/JSC151021097P
ER  - 

@article{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Novaković, Irena T. and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
abstract = "A series of sixteen novel substituted piperidines and (2-methoxyphenyl)piperazines were synthesized, starting from the key intermediates 1-(2-methoxyphenyl)-4-(piperidin-4-yl)piperazine and 1-(2-methoxyphenyl)-4-[(piperidin-4-yl)methyl] piperazine. Biological evaluation of the synthesized compounds was illustrated by seven compounds, of which 1-(2-methoxyphenyl)-4-{[1-(2-nitrobenzyl) piperidin-4-yl] methyl} piperazine had the highest affinity for the dopamine D-2 receptor. For all seven selected compounds, docking analysis was performed in order to establish their structure-to-activity relationship.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines",
volume = "81",
number = "4",
pages = "347-356",
doi = "10.2298/JSC151021097P"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Novaković, I. T., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 81(4), 347-356.
https://doi.org/10.2298/JSC151021097P

Penjišević J, Šukalović V, Andrić D, Roglić G, Novaković IT, Šoškić V, Kostić-Rajačić S. Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines. in Journal of the Serbian Chemical Society. 2016;81(4):347-356.
doi:10.2298/JSC151021097P .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Novaković, Irena T., Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis, biological evaluation and docking analysis of substituted piperidines and (2-methoxyphenyl)piperazines" in Journal of the Serbian Chemical Society, 81, no. 4 (2016):347-356,
https://doi.org/10.2298/JSC151021097P . .

TY  - JOUR
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2286
AB  - Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands
VL  - 349
IS  - 8
SP  - 614
EP  - 626
DO  - 10.1002/ardp.201600081
ER  - 

@article{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
abstract = "Sixteen new 1-(2-methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines were synthesized to be used as probes for mapping the dopamine D-2 receptor (D(2)DAR) arylpiperazine binding site. All compounds were evaluated for their affinity toward D(2)DAR in an in vitro competitive displacement assay. The most active one was 1-(2-methoxyphenyl)-4-{[1-(3-nitrophenethyl)piperidin-4-yl]methyl}piperazine (25) with an affinity of K-i = 54 nM. Docking analysis was conducted on all herein described compounds, whereas molecular dynamic simulation was performed on ligand 25 to establish its mode of interaction with D(2)DAR. Two possible docking orientations are proposed; the one with a salt bridge between the piperidine moiety and Asp114 of D(2)DAR is more stable.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands",
volume = "349",
number = "8",
pages = "614-626",
doi = "10.1002/ardp.201600081"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 349(8), 614-626.
https://doi.org/10.1002/ardp.201600081

Penjišević J, Šukalović V, Andrić D, Roglić G, Šoškić V, Kostić-Rajačić S. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands. in Archiv der Pharmazie. 2016;349(8):614-626.
doi:10.1002/ardp.201600081 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-phenethylpiperidin-4-yl)piperazines and 1-(2-Methoxyphenyl)-4-[(1-phenethylpiperidin-4-yl)methyl]piperazines as Dopaminergic Ligands" in Archiv der Pharmazie, 349, no. 8 (2016):614-626,
https://doi.org/10.1002/ardp.201600081 . .

TY  - DATA
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Novaković, Irena T.
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3630
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3630
ER  - 

@misc{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Novaković, Irena T. and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3630"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Novaković, I. T., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade..
https://hdl.handle.net/21.15107/rcub_cherry_3630

Penjišević J, Šukalović V, Andrić D, Roglić G, Novaković IT, Šoškić V, Kostić-Rajačić S. Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P. in Journal of the Serbian Chemical Society. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3630 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Novaković, Irena T., Šoškić, Vukić, Kostić-Rajačić, Slađana, "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Novaković, I. T.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological Evaluation and Docking Analysis of Substituted Piperidines and (2-Methoxyphenyl)Piperazines. Journal of the Serbian Chemical Society 2016, 81 (4), 347–356. https://doi.org/10.2298/JSC151021097P" in Journal of the Serbian Chemical Society (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3630 .

TY  - DATA
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Andrić, Deana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Kostić-Rajačić, Slađana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3631
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3631
ER  - 

@misc{
author = "Penjišević, Jelena and Šukalović, Vladimir and Andrić, Deana and Roglić, Goran and Šoškić, Vukić and Kostić-Rajačić, Slađana",
year = "2016",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3631"
}

Penjišević, J., Šukalović, V., Andrić, D., Roglić, G., Šoškić, V.,& Kostić-Rajačić, S.. (2016). Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3631

Penjišević J, Šukalović V, Andrić D, Roglić G, Šoškić V, Kostić-Rajačić S. Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081. in Archiv der Pharmazie. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3631 .

Penjišević, Jelena, Šukalović, Vladimir, Andrić, Deana, Roglić, Goran, Šoškić, Vukić, Kostić-Rajačić, Slađana, "Supplementary data for the article: Penjišević, J. Z.; Šukalović, V. V.; Andrić, D. B.; Roglić, G. M.; Šoškić, V.; Kostić-Rajačić, S. V. Synthesis, Biological, and Computational Evaluation of Substituted 1-(2-Methoxyphenyl)-4-(1-Phenethylpiperidin-4-Yl)Piperazines and 1-(2-Methoxyphenyl)-4-[(1-Phenethylpiperidin-4-Yl)Methyl]Piperazines as Dopaminergic Ligands. Archiv der Pharmazie 2016, 614–626. https://doi.org/10.1002/ardp.201600081" in Archiv der Pharmazie (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3631 .

TY  - JOUR
AU  - Popović-Djordjević, Jelena
AU  - Stepanović, Stepan
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Ivanović, Milovan
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/115
AB  - It was found that NaH suspension in DMSO was highly activated when reacted with an alcohol. The in situ generated NaH/alkoxide mixture permitted very rapid and complete deprotonation and acylation of various cyclic ketones with alkyl carbonates at ambient temperature. Activated NaH/alkoxide in DMSO is particularly effective in Dieckmann condensations, where it affords 5- and 6-membered carbocyclic or N-containing heterocyclic β-keto esters in high yields. A heterocyclic Dieckmann condensation was performed on a molar scale, demonstrating the scalability of the procedure. Besides, DMSO is non-toxic, relatively inexpensive and environmentally benign solvent. © 2016 The Author(s). Published by Taylor & Francis.
T2  - Green Chemistry Letters and Reviews
T1  - High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide
VL  - 9
IS  - 1
SP  - 61
EP  - 68
DO  - 10.1080/17518253.2016.1145744
ER  - 

@article{
author = "Popović-Djordjević, Jelena and Stepanović, Stepan and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan",
year = "2016",
abstract = "It was found that NaH suspension in DMSO was highly activated when reacted with an alcohol. The in situ generated NaH/alkoxide mixture permitted very rapid and complete deprotonation and acylation of various cyclic ketones with alkyl carbonates at ambient temperature. Activated NaH/alkoxide in DMSO is particularly effective in Dieckmann condensations, where it affords 5- and 6-membered carbocyclic or N-containing heterocyclic β-keto esters in high yields. A heterocyclic Dieckmann condensation was performed on a molar scale, demonstrating the scalability of the procedure. Besides, DMSO is non-toxic, relatively inexpensive and environmentally benign solvent. © 2016 The Author(s). Published by Taylor & Francis.",
journal = "Green Chemistry Letters and Reviews",
title = "High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide",
volume = "9",
number = "1",
pages = "61-68",
doi = "10.1080/17518253.2016.1145744"
}

Popović-Djordjević, J., Stepanović, S., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (2016). High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide. in Green Chemistry Letters and Reviews, 9(1), 61-68.
https://doi.org/10.1080/17518253.2016.1145744

Popović-Djordjević J, Stepanović S, Došen-Mićović L, Ivanović ER, Ivanović M. High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide. in Green Chemistry Letters and Reviews. 2016;9(1):61-68.
doi:10.1080/17518253.2016.1145744 .

Popović-Djordjević, Jelena, Stepanović, Stepan, Došen-Mićović, Ljiljana, Ivanović, Evica R., Ivanović, Milovan, "High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide" in Green Chemistry Letters and Reviews, 9, no. 1 (2016):61-68,
https://doi.org/10.1080/17518253.2016.1145744 . .

TY  - JOUR
AU  - Popović-Djordjević, Jelena
AU  - Stepanović, Stepan
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Ivanović, Milovan
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3522
T2  - Green Chemistry Letters and Reviews
T1  - Supplementary data for the article: Popović-Djordjević, J.; Stepanović, S.; Došen-Mićović, L.; Ivanović, E.; Ivanović, M. D. High-Yielding Method for Preparation of Carbocyclic or N-Containing Heterocyclic β-Keto Esters Using in Situ Activated Sodium Hydride in Dimethyl Sulphoxide. Green Chemistry Letters and Reviews 2016, 9 (1), 61–68. https://doi.org/10.1080/17518253.2016.1145744
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3522
ER  - 

@article{
author = "Popović-Djordjević, Jelena and Stepanović, Stepan and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan",
year = "2016",
journal = "Green Chemistry Letters and Reviews",
title = "Supplementary data for the article: Popović-Djordjević, J.; Stepanović, S.; Došen-Mićović, L.; Ivanović, E.; Ivanović, M. D. High-Yielding Method for Preparation of Carbocyclic or N-Containing Heterocyclic β-Keto Esters Using in Situ Activated Sodium Hydride in Dimethyl Sulphoxide. Green Chemistry Letters and Reviews 2016, 9 (1), 61–68. https://doi.org/10.1080/17518253.2016.1145744",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3522"
}

Popović-Djordjević, J., Stepanović, S., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (2016). Supplementary data for the article: Popović-Djordjević, J.; Stepanović, S.; Došen-Mićović, L.; Ivanović, E.; Ivanović, M. D. High-Yielding Method for Preparation of Carbocyclic or N-Containing Heterocyclic β-Keto Esters Using in Situ Activated Sodium Hydride in Dimethyl Sulphoxide. Green Chemistry Letters and Reviews 2016, 9 (1), 61–68. https://doi.org/10.1080/17518253.2016.1145744. in Green Chemistry Letters and Reviews.
https://hdl.handle.net/21.15107/rcub_cherry_3522

Popović-Djordjević J, Stepanović S, Došen-Mićović L, Ivanović ER, Ivanović M. Supplementary data for the article: Popović-Djordjević, J.; Stepanović, S.; Došen-Mićović, L.; Ivanović, E.; Ivanović, M. D. High-Yielding Method for Preparation of Carbocyclic or N-Containing Heterocyclic β-Keto Esters Using in Situ Activated Sodium Hydride in Dimethyl Sulphoxide. Green Chemistry Letters and Reviews 2016, 9 (1), 61–68. https://doi.org/10.1080/17518253.2016.1145744. in Green Chemistry Letters and Reviews. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3522 .

Popović-Djordjević, Jelena, Stepanović, Stepan, Došen-Mićović, Ljiljana, Ivanović, Evica R., Ivanović, Milovan, "Supplementary data for the article: Popović-Djordjević, J.; Stepanović, S.; Došen-Mićović, L.; Ivanović, E.; Ivanović, M. D. High-Yielding Method for Preparation of Carbocyclic or N-Containing Heterocyclic β-Keto Esters Using in Situ Activated Sodium Hydride in Dimethyl Sulphoxide. Green Chemistry Letters and Reviews 2016, 9 (1), 61–68. https://doi.org/10.1080/17518253.2016.1145744" in Green Chemistry Letters and Reviews (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3522 .

TY  - JOUR
AU  - Jevtić, Ivana I.
AU  - Došen-Mićović, Ljiljana
AU  - Ivanović, Evica R.
AU  - Ivanović, Milovan
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1935
AB  - An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide
VL  - 48
IS  - 10
SP  - 1550
EP  - 1560
DO  - 10.1055/s-0035-1561405
ER  - 

@article{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan",
year = "2016",
abstract = "An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. -Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide",
volume = "48",
number = "10",
pages = "1550-1560",
doi = "10.1055/s-0035-1561405"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (2016). Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. in Synthesis, Stuttgart
Georg Thieme Verlag Kg, Stuttgart., 48(10), 1550-1560.
https://doi.org/10.1055/s-0035-1561405

Jevtić II, Došen-Mićović L, Ivanović ER, Ivanović M. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. in Synthesis, Stuttgart. 2016;48(10):1550-1560.
doi:10.1055/s-0035-1561405 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Ivanović, Milovan, "Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide" in Synthesis, Stuttgart, 48, no. 10 (2016):1550-1560,
https://doi.org/10.1055/s-0035-1561405 . .