TY  - JOUR
AU  - Šegan, Sandra B.
AU  - Jevtić, Ivana I.
AU  - Tosti, Tomislav
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Kostić-Rajačić, Slađana
AU  - Milojković-Opsenica, Dušanka
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5649
AB  - Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-
layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of the
piperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diaste-
reomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constant
of fentanyl were also determined by the same method, as a reference. The physicochemical property, lip-
ophilicity, expressed as retention indices RM
0 , b, and C0, as well as PC1, was determined and correlated with in
silico values. Ionization constants were determined on the basis of the relationships between analyte’s retention
expressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, were
subjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to provide
basic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeation
was investigated in the function of experimentally obtained values of lipophilicity, polar surface area and mo-
lecular weight. In general, results of the present research corroborate well with previously determined anti-
nociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, another
set of important parameters should be taken into account when designing new derivatives of C-3 substituted
fentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLC
can be considered as a valuable asset in the ligand-based drug design
PB  - Elsevier
T2  - Journal of Chromatography B
T1  - Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography
VL  - 1211
SP  - 123481
DO  - 10.1016/j.jchromb.2022.123481
ER  - 

@article{
author = "Šegan, Sandra B. and Jevtić, Ivana I. and Tosti, Tomislav and Penjišević, Jelena and Šukalović, Vladimir and Kostić-Rajačić, Slađana and Milojković-Opsenica, Dušanka",
year = "2022",
abstract = "Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-
layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of the
piperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diaste-
reomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constant
of fentanyl were also determined by the same method, as a reference. The physicochemical property, lip-
ophilicity, expressed as retention indices RM
0 , b, and C0, as well as PC1, was determined and correlated with in
silico values. Ionization constants were determined on the basis of the relationships between analyte’s retention
expressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, were
subjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to provide
basic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeation
was investigated in the function of experimentally obtained values of lipophilicity, polar surface area and mo-
lecular weight. In general, results of the present research corroborate well with previously determined anti-
nociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, another
set of important parameters should be taken into account when designing new derivatives of C-3 substituted
fentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLC
can be considered as a valuable asset in the ligand-based drug design",
publisher = "Elsevier",
journal = "Journal of Chromatography B",
title = "Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography",
volume = "1211",
pages = "123481",
doi = "10.1016/j.jchromb.2022.123481"
}

Šegan, S. B., Jevtić, I. I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B
Elsevier., 1211, 123481.
https://doi.org/10.1016/j.jchromb.2022.123481

Šegan SB, Jevtić II, Tosti T, Penjišević J, Šukalović V, Kostić-Rajačić S, Milojković-Opsenica D. Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B. 2022;1211:123481.
doi:10.1016/j.jchromb.2022.123481 .

Šegan, Sandra B., Jevtić, Ivana I., Tosti, Tomislav, Penjišević, Jelena, Šukalović, Vladimir, Kostić-Rajačić, Slađana, Milojković-Opsenica, Dušanka, "Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography" in Journal of Chromatography B, 1211 (2022):123481,
https://doi.org/10.1016/j.jchromb.2022.123481 . .

TY  - DATA
AU  - Šegan, Sandra B.
AU  - Jevtić, Ivana I.
AU  - Tosti, Tomislav
AU  - Penjišević, Jelena
AU  - Šukalović, Vladimir
AU  - Kostić-Rajačić, Slađana
AU  - Milojković-Opsenica, Dušanka
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5650
AB  - Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of thepiperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diaste-reomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constantof fentanyl were also determined by the same method, as a reference. The physicochemical property, lip-ophilicity, expressed as retention indices RM0 , b, and C0, as well as PC1, was determined and correlated with insilico values. Ionization constants were determined on the basis of the relationships between analyte’s retentionexpressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, weresubjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to providebasic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeationwas investigated in the function of experimentally obtained values of lipophilicity, polar surface area and mo-lecular weight. In general, results of the present research corroborate well with previously determined anti-nociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, anotherset of important parameters should be taken into account when designing new derivatives of C-3 substitutedfentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLCcan be considered as a valuable asset in the ligand-based drug design
PB  - Elsevier
T2  - Journal of Chromatography B
T1  - Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481
VL  - 1211
SP  - 123481
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5650
ER  - 

@misc{
author = "Šegan, Sandra B. and Jevtić, Ivana I. and Tosti, Tomislav and Penjišević, Jelena and Šukalović, Vladimir and Kostić-Rajačić, Slađana and Milojković-Opsenica, Dušanka",
year = "2022",
abstract = "Lipophilicity and ionization constant of sixteen fentanyl analogues were investigated by reversed-phase thin-layer chromatography (RP-TLC). Fourteen compounds have nitrogen containing groups at C-3 position of thepiperidine ring and two compounds are 3-carbomethoxy derivatives of fentanyl. Among them, five are diaste-reomeric cis/trans couples and six novel trans diastereomers. In addition, the lipophilicity and ionization constantof fentanyl were also determined by the same method, as a reference. The physicochemical property, lip-ophilicity, expressed as retention indices RM0 , b, and C0, as well as PC1, was determined and correlated with insilico values. Ionization constants were determined on the basis of the relationships between analyte’s retentionexpressed as RF and mobile phase pH. Calculated structural descriptors together with the retention indices, weresubjected to the principal component analysis – PCA and hierarchical cluster analysis – HCA, in order to providebasic insights into the similarities among the studied compounds. The blood – brain barrier (BBB) permeationwas investigated in the function of experimentally obtained values of lipophilicity, polar surface area and mo-lecular weight. In general, results of the present research corroborate well with previously determined anti-nociceptive activities of the investigated compounds, pointing out that besides the cis/trans isomerism, anotherset of important parameters should be taken into account when designing new derivatives of C-3 substitutedfentanyl, especially lipophilicity, voluminosity and HBD/A character of the substituents. Accordingly, RP-TLCcan be considered as a valuable asset in the ligand-based drug design",
publisher = "Elsevier",
journal = "Journal of Chromatography B",
title = "Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481",
volume = "1211",
pages = "123481",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5650"
}

Šegan, S. B., Jevtić, I. I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481. in Journal of Chromatography B
Elsevier., 1211, 123481.
https://hdl.handle.net/21.15107/rcub_cherry_5650

Šegan SB, Jevtić II, Tosti T, Penjišević J, Šukalović V, Kostić-Rajačić S, Milojković-Opsenica D. Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481. in Journal of Chromatography B. 2022;1211:123481.
https://hdl.handle.net/21.15107/rcub_cherry_5650 .

Šegan, Sandra B., Jevtić, Ivana I., Tosti, Tomislav, Penjišević, Jelena, Šukalović, Vladimir, Kostić-Rajačić, Slađana, Milojković-Opsenica, Dušanka, "Supplementary material for: Šegan, S., Jevtić, I., Tosti, T., Penjišević, J., Šukalović, V., Kostić-Rajačić, S.,& Milojković-Opsenica, D.. (2022). Determination of lipophilicity and ionization of fentanyl and its 3‑substituted analogs by reversed-phase thin-layer chromatography. in Journal of Chromatography B Elsevier., 1211, 123481. https://doi.org/10.1016/j.jchromb.2022.123481" in Journal of Chromatography B, 1211 (2022):123481,
https://hdl.handle.net/21.15107/rcub_cherry_5650 .

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  - JOUR
AU  - Jevtić, Ivana I.
AU  - Lai, Thu Hang
AU  - Penjišević, Jelena
AU  - Dukić-Stefanović, Slađana
AU  - Andrić, Deana
AU  - Brust, Peter
AU  - Kostić-Rajačić, Slađana
AU  - Teodoro, Rodrigo
PY  - 2020
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4272
AB  - Herein, we report on the synthesis and pharmacological evaluation of ten novel fluorinated cinnamylpiperazines as potential monoamine oxidase B (MAO-B) ligands. The designed derivatives consist of either cinnamyl or 2-fluorocinnamyl moieties connected to 2-fluoropyridylpiperazines. The three-step synthesis starting from commercially available piperazine afforded the final products in overall yields between 9% and 29%. An in vitro competitive binding assay using l-[3H]Deprenyl as radioligand was developed and the MAO-B binding affinities of the synthesized derivatives were assessed. Docking studies revealed that the compounds 8–17 were stabilized in both MAO-B entrance and substrate cavities, thus resembling the binding pose of l-Deprenyl. Although our results revealed that the novel fluorinated cinnamylpiperazines 8–17 do not possess sufficient MAO-B binding affinity to be eligible as positron emission tomography (PET) agents, the herein developed binding assay and the insights gained within our docking studies will certainly pave the way for further development of MAO-B ligands.
PB  - MDPI
T2  - Molecules
T1  - Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding
VL  - 25
IS  - 21
SP  - 4941
DO  - 10.3390/molecules25214941
ER  - 

@article{
author = "Jevtić, Ivana I. and Lai, Thu Hang and Penjišević, Jelena and Dukić-Stefanović, Slađana and Andrić, Deana and Brust, Peter and Kostić-Rajačić, Slađana and Teodoro, Rodrigo",
year = "2020",
abstract = "Herein, we report on the synthesis and pharmacological evaluation of ten novel fluorinated cinnamylpiperazines as potential monoamine oxidase B (MAO-B) ligands. The designed derivatives consist of either cinnamyl or 2-fluorocinnamyl moieties connected to 2-fluoropyridylpiperazines. The three-step synthesis starting from commercially available piperazine afforded the final products in overall yields between 9% and 29%. An in vitro competitive binding assay using l-[3H]Deprenyl as radioligand was developed and the MAO-B binding affinities of the synthesized derivatives were assessed. Docking studies revealed that the compounds 8–17 were stabilized in both MAO-B entrance and substrate cavities, thus resembling the binding pose of l-Deprenyl. Although our results revealed that the novel fluorinated cinnamylpiperazines 8–17 do not possess sufficient MAO-B binding affinity to be eligible as positron emission tomography (PET) agents, the herein developed binding assay and the insights gained within our docking studies will certainly pave the way for further development of MAO-B ligands.",
publisher = "MDPI",
journal = "Molecules",
title = "Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding",
volume = "25",
number = "21",
pages = "4941",
doi = "10.3390/molecules25214941"
}

Jevtić, I. I., Lai, T. H., Penjišević, J., Dukić-Stefanović, S., Andrić, D., Brust, P., Kostić-Rajačić, S.,& Teodoro, R.. (2020). Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding. in Molecules
MDPI., 25(21), 4941.
https://doi.org/10.3390/molecules25214941

Jevtić II, Lai TH, Penjišević J, Dukić-Stefanović S, Andrić D, Brust P, Kostić-Rajačić S, Teodoro R. Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding. in Molecules. 2020;25(21):4941.
doi:10.3390/molecules25214941 .

Jevtić, Ivana I., Lai, Thu Hang, Penjišević, Jelena, Dukić-Stefanović, Slađana, Andrić, Deana, Brust, Peter, Kostić-Rajačić, Slađana, Teodoro, Rodrigo, "Newly Synthesized Fluorinated Cinnamylpiperazines Possessing Low In Vitro MAO-B Binding" in Molecules, 25, no. 21 (2020):4941,
https://doi.org/10.3390/molecules25214941 . .

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  - THES
AU  - Jevtić, Ivana I.
PY  - 2020
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=7699
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:22906/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=24288009
UR  - https://nardus.mpn.gov.rs/handle/123456789/17614
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/4372
AB  - U okviru ove disertacije dizajnirano je 30 anilidopipredina, analoga jakog -opioidnog agonista i kliničkog analgetika fentanila. Razvijen je efikasan sintetički put za njihovo dobijanje, a sintetisana jedinjenja mogu se podeliti u dve serije. U okviru prve serije sintetisano je 13 novih analoga fentanila sa različitim azotnim grupama u položaju C3 piperidinskog prstena. Takođe je optimizovana sinteza dva prethodno sintetisana biciklična analoga fentanila. Jedinjenja prve serije predstavljaju prve poznate analoge fentanila sa azotnim grupama u položaju C3. U okviru druge serije sintetisano je 15 novih analoga fentanila, koji su u položaju N1 povezani sa pojedinim N-arilpiperazinima preko linearnih alkil mostova različitih dužina. Jedinjenja druge serije dizajnirana su da budu potencijalni heterobivalenti ligandi, jer sadrže anilidopiperidinsko jezgro fentanila kao -opioidnu agonističku farmakoforu, a N-arilpiperazin kao D2-dopaminergičku, agonističku farmakoforu.Analgetička aktivnost svih 30 jedinjenja ispitana je in vivo. Samo četiri jedinjenja, sva iz prve serije, pokazala su analgetičku aktivnost. Najaktivnije jedinjenje, oko 1,8 puta manje aktivno od fentanila, karakterišu brzo i kratko dejstvo analgetičkog efekta, pa se stoga može potencijalno iskoristiti u različitim farmacutskim formulacijama za tretman bola. Afinitet vezivanja jedinjenja druge serije za dopaminergčke D2 receptore ispitan je in vitro testovima kompeticije koristeći 3H spiperon kao radioaktivni ligand. Odsustvo analgetičke aktivnosti i slab afinitet vezivanja za dopaminergičke D2 receptore, ukazuje da jedinjenja druge serije ne mogu poslužiti kao heterobivalentni ligandi.Preliminarna doking analiza urađena je za jedinjenja koja su pokazala farmakološku aktivnost.
AB  - This PhD thesis encompasses the design of 30 anilidopiperidines, as analogues of potent -opioid agonist and clinical analgesic, fentanyl. All compounds were prepared by the novel and effcient synthetic routes, and can be divided in two series. In the first series, 13 new analogues of fentanyl with various nitrogen groups in the C3 position of the piperidine ring were synthesized. In addition, the synthesis of two bicyclic analogues of fentanyl, previously synthesized by our group, was optimized. The compounds of the first series represent the first known fentanyl analogues possessing any nitrogen substituent at C3 position of the piperidine ring. The second series involved preparation of 15 new compounds consisting of fentanyl moiety and several arylpiperazine groups joined by the respective secondary nitrogens, via the variable-length alkyl linkers. The compounds were designed to be potential heterobivalent ligands, since they include both the fentanyl core, as the -opioid agonist pharmacophore, and N-arylpiperazine moiety as the D2-dopaminergic agonist pharmacophore.The analgesic activity of 30 compounds was tested in vivo. Only four compounds, all from the first series, showed analgesic activity. The most potent of them was 1.8 times less potent analgesic than fentanyl, with fast onset and short duration of analgesic effect, which makes this compound potentially suitable for different pharmacological formulation in the pain treatment. Binding affinity of the compounds of the second series towards dopaminergic D2 receptors was determined by in vitro competitive assay, using 3H spiperon as radioactive ligand. Compounds of the second series were found to be inactive as analgesics and with low affinity towards dopaminergic D2 receptors. Therefore, the compounds do not represent heterobivalent ligands.Preliminary docking analysis was performed for the pharmacologically active compounds.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Sinteza, farmakološko ispitivanje i doking analiza novih anilidopiperidina
UR  - https://hdl.handle.net/21.15107/rcub_nardus_17614
ER  - 

@phdthesis{
author = "Jevtić, Ivana I.",
year = "2020",
abstract = "U okviru ove disertacije dizajnirano je 30 anilidopipredina, analoga jakog -opioidnog agonista i kliničkog analgetika fentanila. Razvijen je efikasan sintetički put za njihovo dobijanje, a sintetisana jedinjenja mogu se podeliti u dve serije. U okviru prve serije sintetisano je 13 novih analoga fentanila sa različitim azotnim grupama u položaju C3 piperidinskog prstena. Takođe je optimizovana sinteza dva prethodno sintetisana biciklična analoga fentanila. Jedinjenja prve serije predstavljaju prve poznate analoge fentanila sa azotnim grupama u položaju C3. U okviru druge serije sintetisano je 15 novih analoga fentanila, koji su u položaju N1 povezani sa pojedinim N-arilpiperazinima preko linearnih alkil mostova različitih dužina. Jedinjenja druge serije dizajnirana su da budu potencijalni heterobivalenti ligandi, jer sadrže anilidopiperidinsko jezgro fentanila kao -opioidnu agonističku farmakoforu, a N-arilpiperazin kao D2-dopaminergičku, agonističku farmakoforu.Analgetička aktivnost svih 30 jedinjenja ispitana je in vivo. Samo četiri jedinjenja, sva iz prve serije, pokazala su analgetičku aktivnost. Najaktivnije jedinjenje, oko 1,8 puta manje aktivno od fentanila, karakterišu brzo i kratko dejstvo analgetičkog efekta, pa se stoga može potencijalno iskoristiti u različitim farmacutskim formulacijama za tretman bola. Afinitet vezivanja jedinjenja druge serije za dopaminergčke D2 receptore ispitan je in vitro testovima kompeticije koristeći 3H spiperon kao radioaktivni ligand. Odsustvo analgetičke aktivnosti i slab afinitet vezivanja za dopaminergičke D2 receptore, ukazuje da jedinjenja druge serije ne mogu poslužiti kao heterobivalentni ligandi.Preliminarna doking analiza urađena je za jedinjenja koja su pokazala farmakološku aktivnost., This PhD thesis encompasses the design of 30 anilidopiperidines, as analogues of potent -opioid agonist and clinical analgesic, fentanyl. All compounds were prepared by the novel and effcient synthetic routes, and can be divided in two series. In the first series, 13 new analogues of fentanyl with various nitrogen groups in the C3 position of the piperidine ring were synthesized. In addition, the synthesis of two bicyclic analogues of fentanyl, previously synthesized by our group, was optimized. The compounds of the first series represent the first known fentanyl analogues possessing any nitrogen substituent at C3 position of the piperidine ring. The second series involved preparation of 15 new compounds consisting of fentanyl moiety and several arylpiperazine groups joined by the respective secondary nitrogens, via the variable-length alkyl linkers. The compounds were designed to be potential heterobivalent ligands, since they include both the fentanyl core, as the -opioid agonist pharmacophore, and N-arylpiperazine moiety as the D2-dopaminergic agonist pharmacophore.The analgesic activity of 30 compounds was tested in vivo. Only four compounds, all from the first series, showed analgesic activity. The most potent of them was 1.8 times less potent analgesic than fentanyl, with fast onset and short duration of analgesic effect, which makes this compound potentially suitable for different pharmacological formulation in the pain treatment. Binding affinity of the compounds of the second series towards dopaminergic D2 receptors was determined by in vitro competitive assay, using 3H spiperon as radioactive ligand. Compounds of the second series were found to be inactive as analgesics and with low affinity towards dopaminergic D2 receptors. Therefore, the compounds do not represent heterobivalent ligands.Preliminary docking analysis was performed for the pharmacologically active compounds.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Sinteza, farmakološko ispitivanje i doking analiza novih anilidopiperidina",
url = "https://hdl.handle.net/21.15107/rcub_nardus_17614"
}

Jevtić, I. I.. (2020). Sinteza, farmakološko ispitivanje i doking analiza novih anilidopiperidina. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_17614

Jevtić II. Sinteza, farmakološko ispitivanje i doking analiza novih anilidopiperidina. in Универзитет у Београду. 2020;.
https://hdl.handle.net/21.15107/rcub_nardus_17614 .

Jevtić, Ivana I., "Sinteza, farmakološko ispitivanje i doking analiza novih anilidopiperidina" in Универзитет у Београду (2020),
https://hdl.handle.net/21.15107/rcub_nardus_17614 .

TY  - JOUR
AU  - Jevtić, Ivana I.
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/123456789/4211
AB  - Background: 4-Anilidopiperidine class of synthetic opioid analgesics, with it’s representative fentanyl, are by far the most potent and clinically significant for the treatment of the severe chronic and surgical pain. However, side effects of μ-opioids are often quite serious. In order to improve the pharmacological profile of this class of opioid analgesics, a novel fentanyl analogs were designed, synthesized and evaluated in vivo for their antinociceptive activity. Methods: The title compounds were prepared using known synthetic transformations, including N-bromoacetamide mediated Hofmann rearrangement, highly selective carbamate cleavage with trimethylsilyl iodide and dehydration of carboxamide group to nitrile in the presence of SOCl2. The antinociceptive activity of the synthesized compounds was determined by tail-immersion and formalin test. Results: The scalable synthetic route towards novel fentanyl analogs bearing nitrogen groups in position C3 of piperidine ring is designed. In addition, Hofmann rearrangement was substantially improved for the more efficient synthesis of previously published 3-substituted fentanyl analogs. The series of ten fentanyl analogs was tested in vivo for their antinociceptive activity. The most potent compound of the series was found to be cis-4, based on the determined ED50 values in tail-immersion test. Conclusion: Of ten compounds tested for their antinociceptive activity, compound cis-4 is characterized by high potency, rapid beginning and short duration of action and due to this might be incorporated in different pharmaceutical forms.
PB  - Springer
T2  - Pharmacological Reports
T1  - Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines
VL  - 72
IS  - 4
SP  - 1069
EP  - 1075
DO  - 10.1007/s43440-020-00121-2
ER  - 

@article{
author = "Jevtić, Ivana I. and Savić-Vujović, Katarina and Srebro, Dragana and Vučković, Sonja M. and Ivanović, Milovan and Kostić-Rajačić, Slađana",
year = "2020",
abstract = "Background: 4-Anilidopiperidine class of synthetic opioid analgesics, with it’s representative fentanyl, are by far the most potent and clinically significant for the treatment of the severe chronic and surgical pain. However, side effects of μ-opioids are often quite serious. In order to improve the pharmacological profile of this class of opioid analgesics, a novel fentanyl analogs were designed, synthesized and evaluated in vivo for their antinociceptive activity. Methods: The title compounds were prepared using known synthetic transformations, including N-bromoacetamide mediated Hofmann rearrangement, highly selective carbamate cleavage with trimethylsilyl iodide and dehydration of carboxamide group to nitrile in the presence of SOCl2. The antinociceptive activity of the synthesized compounds was determined by tail-immersion and formalin test. Results: The scalable synthetic route towards novel fentanyl analogs bearing nitrogen groups in position C3 of piperidine ring is designed. In addition, Hofmann rearrangement was substantially improved for the more efficient synthesis of previously published 3-substituted fentanyl analogs. The series of ten fentanyl analogs was tested in vivo for their antinociceptive activity. The most potent compound of the series was found to be cis-4, based on the determined ED50 values in tail-immersion test. Conclusion: Of ten compounds tested for their antinociceptive activity, compound cis-4 is characterized by high potency, rapid beginning and short duration of action and due to this might be incorporated in different pharmaceutical forms.",
publisher = "Springer",
journal = "Pharmacological Reports",
title = "Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines",
volume = "72",
number = "4",
pages = "1069-1075",
doi = "10.1007/s43440-020-00121-2"
}

Jevtić, I. I., Savić-Vujović, K., Srebro, D., Vučković, S. M., Ivanović, M.,& Kostić-Rajačić, S.. (2020). Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines. in Pharmacological Reports
Springer., 72(4), 1069-1075.
https://doi.org/10.1007/s43440-020-00121-2

Jevtić II, Savić-Vujović K, Srebro D, Vučković SM, Ivanović M, Kostić-Rajačić S. Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines. in Pharmacological Reports. 2020;72(4):1069-1075.
doi:10.1007/s43440-020-00121-2 .

Jevtić, Ivana I., Savić-Vujović, Katarina, Srebro, Dragana, Vučković, Sonja M., Ivanović, Milovan, Kostić-Rajačić, Slađana, "Synthesis and pharmacological evaluation of novel cis and trans 3-substituted anilidopiperidines" in Pharmacological Reports, 72, no. 4 (2020):1069-1075,
https://doi.org/10.1007/s43440-020-00121-2 . .

TY  - DATA
AU  - Jevtić, Ivana I.
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/123456789/4212
PB  - Springer
T2  - Pharmacological Reports
T1  - Supplementary data for the article: Jevtić, I. I.; Savić Vujović, K.; Srebro, D.; Vučković, S.; Ivanović, M. D.; Kostić-Rajačić, S. V. Synthesis and Pharmacological Evaluation of Novel Cis and Trans 3-Substituted Anilidopiperidines. Pharmacol. Rep 2020, 72 (4), 1069–1075. https://doi.org/10.1007/s43440-020-00121-2
UR  - https://hdl.handle.net/21.15107/rcub_cherry_4212
ER  - 

@misc{
author = "Jevtić, Ivana I. and Savić-Vujović, Katarina and Srebro, Dragana and Vučković, Sonja M. and Ivanović, Milovan and Kostić-Rajačić, Slađana",
year = "2020",
publisher = "Springer",
journal = "Pharmacological Reports",
title = "Supplementary data for the article: Jevtić, I. I.; Savić Vujović, K.; Srebro, D.; Vučković, S.; Ivanović, M. D.; Kostić-Rajačić, S. V. Synthesis and Pharmacological Evaluation of Novel Cis and Trans 3-Substituted Anilidopiperidines. Pharmacol. Rep 2020, 72 (4), 1069–1075. https://doi.org/10.1007/s43440-020-00121-2",
url = "https://hdl.handle.net/21.15107/rcub_cherry_4212"
}

Jevtić, I. I., Savić-Vujović, K., Srebro, D., Vučković, S. M., Ivanović, M.,& Kostić-Rajačić, S.. (2020). Supplementary data for the article: Jevtić, I. I.; Savić Vujović, K.; Srebro, D.; Vučković, S.; Ivanović, M. D.; Kostić-Rajačić, S. V. Synthesis and Pharmacological Evaluation of Novel Cis and Trans 3-Substituted Anilidopiperidines. Pharmacol. Rep 2020, 72 (4), 1069–1075. https://doi.org/10.1007/s43440-020-00121-2. in Pharmacological Reports
Springer..
https://hdl.handle.net/21.15107/rcub_cherry_4212

Jevtić II, Savić-Vujović K, Srebro D, Vučković SM, Ivanović M, Kostić-Rajačić S. Supplementary data for the article: Jevtić, I. I.; Savić Vujović, K.; Srebro, D.; Vučković, S.; Ivanović, M. D.; Kostić-Rajačić, S. V. Synthesis and Pharmacological Evaluation of Novel Cis and Trans 3-Substituted Anilidopiperidines. Pharmacol. Rep 2020, 72 (4), 1069–1075. https://doi.org/10.1007/s43440-020-00121-2. in Pharmacological Reports. 2020;.
https://hdl.handle.net/21.15107/rcub_cherry_4212 .

Jevtić, Ivana I., Savić-Vujović, Katarina, Srebro, Dragana, Vučković, Sonja M., Ivanović, Milovan, Kostić-Rajačić, Slađana, "Supplementary data for the article: Jevtić, I. I.; Savić Vujović, K.; Srebro, D.; Vučković, S.; Ivanović, M. D.; Kostić-Rajačić, S. V. Synthesis and Pharmacological Evaluation of Novel Cis and Trans 3-Substituted Anilidopiperidines. Pharmacol. Rep 2020, 72 (4), 1069–1075. https://doi.org/10.1007/s43440-020-00121-2" in Pharmacological Reports (2020),
https://hdl.handle.net/21.15107/rcub_cherry_4212 .

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 . .

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  - 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 . .

TY  - DATA
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/123456789/3523
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synthesis, Stuttgart
T1  - Supplementary data for the article: Jevtić, I. I.; Došen-Mićović, L.; Ivanović, E. R.; Ivanović, M. D. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. Synthesis (Germany) 2016, 48 (10), 1550–1560. https://doi.org/10.1055/s-0035-1561405
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3523
ER  - 

@misc{
author = "Jevtić, Ivana I. and Došen-Mićović, Ljiljana and Ivanović, Evica R. and Ivanović, Milovan",
year = "2016",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synthesis, Stuttgart",
title = "Supplementary data for the article: Jevtić, I. I.; Došen-Mićović, L.; Ivanović, E. R.; Ivanović, M. D. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. Synthesis (Germany) 2016, 48 (10), 1550–1560. https://doi.org/10.1055/s-0035-1561405",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3523"
}

Jevtić, I. I., Došen-Mićović, L., Ivanović, E. R.,& Ivanović, M.. (2016). Supplementary data for the article: Jevtić, I. I.; Došen-Mićović, L.; Ivanović, E. R.; Ivanović, M. D. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. Synthesis (Germany) 2016, 48 (10), 1550–1560. https://doi.org/10.1055/s-0035-1561405. in Synthesis, Stuttgart
Georg Thieme Verlag Kg, Stuttgart..
https://hdl.handle.net/21.15107/rcub_cherry_3523

Jevtić II, Došen-Mićović L, Ivanović ER, Ivanović M. Supplementary data for the article: Jevtić, I. I.; Došen-Mićović, L.; Ivanović, E. R.; Ivanović, M. D. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. Synthesis (Germany) 2016, 48 (10), 1550–1560. https://doi.org/10.1055/s-0035-1561405. in Synthesis, Stuttgart. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3523 .

Jevtić, Ivana I., Došen-Mićović, Ljiljana, Ivanović, Evica R., Ivanović, Milovan, "Supplementary data for the article: Jevtić, I. I.; Došen-Mićović, L.; Ivanović, E. R.; Ivanović, M. D. Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide. Synthesis (Germany) 2016, 48 (10), 1550–1560. https://doi.org/10.1055/s-0035-1561405" in Synthesis, Stuttgart (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3523 .