TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Bogdan, Anca Elena
AU  - Tovilović, Gordana
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1413
AB  - The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling
VL  - 346
IS  - 10
SP  - 708
EP  - 717
DO  - 10.1002/ardp.201300189
ER  - 

@article{
author = "Šukalović, Vladimir and Bogdan, Anca Elena and Tovilović, Gordana and Ignjatović, Đurđica and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2013",
abstract = "The ratio of affinities toward the dopamine D-2 and the 5-hydroxytryptamine 5-HT1A receptors is one of the important parameters that determine the efficiency of antipsychotic drugs. Here, we present the synthesis of ortho-, meta-, and para-N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides and their structure-activity relationship studies on dopamine D-2 and 5-hydroxytryptamine 5-HT1A receptors. It was shown that the biological activity of the described ligands strongly depends on their topology as well as on the nature of the heteroaryl group in the head of the molecules. Docking simulations together with conformational analysis revealed a rational explanation for the ligands' behavior. The molecular model of receptor-ligand interactions described herein provided us with a tool for the rational design of new compounds with a favorable D-2/5-HT1A profile.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling",
volume = "346",
number = "10",
pages = "708-717",
doi = "10.1002/ardp.201300189"
}

Šukalović, V., Bogdan, A. E., Tovilović, G., Ignjatović, Đ., Andrić, D., Kostić-Rajačić, S.,& Šoškić, V.. (2013). N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim., 346(10), 708-717.
https://doi.org/10.1002/ardp.201300189

Šukalović V, Bogdan AE, Tovilović G, Ignjatović Đ, Andrić D, Kostić-Rajačić S, Šoškić V. N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. in Archiv der Pharmazie. 2013;346(10):708-717.
doi:10.1002/ardp.201300189 .

Šukalović, Vladimir, Bogdan, Anca Elena, Tovilović, Gordana, Ignjatović, Đurđica, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, "N-{[2-(4-Phenyl-piperazin-1-yl)-ethyl]-phenyl}-arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling" in Archiv der Pharmazie, 346, no. 10 (2013):708-717,
https://doi.org/10.1002/ardp.201300189 . .

TY  - DATA
AU  - Šukalović, Vladimir
AU  - Bogdan, Anca Elena
AU  - Tovilović, Gordana
AU  - Ignjatović, Đurđica
AU  - Andrić, Deana
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3511
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Archiv der Pharmazie
T1  - Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3511
ER  - 

@misc{
author = "Šukalović, Vladimir and Bogdan, Anca Elena and Tovilović, Gordana and Ignjatović, Đurđica and Andrić, Deana and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2013",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Archiv der Pharmazie",
title = "Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3511"
}

Šukalović, V., Bogdan, A. E., Tovilović, G., Ignjatović, Đ., Andrić, D., Kostić-Rajačić, S.,& Šoškić, V.. (2013). Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189. in Archiv der Pharmazie
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3511

Šukalović V, Bogdan AE, Tovilović G, Ignjatović Đ, Andrić D, Kostić-Rajačić S, Šoškić V. Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189. in Archiv der Pharmazie. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3511 .

Šukalović, Vladimir, Bogdan, Anca Elena, Tovilović, Gordana, Ignjatović, Đurđica, Andrić, Deana, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Supplementary data for article: Šukalović, V.; Bogdan, A. E.; Tovilovic, G.; Ignjatovic, D.; Andrić, D.; Kostić-Rajačić, S.; Šoškić, V. N-{[2-(4-Phenyl-Piperazin-1-Yl)-Ethyl]-Phenyl}-Arylamides with Dopamine D-2 and 5-Hydroxytryptamine 5HT(1A) Activity: Synthesis, Testing, and Molecular Modeling. Archiv der Pharmazie 2013, 346 (10), 708–717. https://doi.org/10.1002/ardp.201300189" in Archiv der Pharmazie (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3511 .

TY  - JOUR
AU  - Šukalović, Vladimir
AU  - Ignjatović, Đurđica
AU  - Tovilović, Gordana
AU  - Andrić, Deana
AU  - Shakib, Kaveh
AU  - Kostić-Rajačić, Slađana
AU  - Šoškić, Vukić
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1302
AB  - It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic and Medicinal Chemistry Letters
T1  - Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors
VL  - 22
IS  - 12
SP  - 3967
EP  - 3972
DO  - 10.1016/j.bmcl.2012.04.098
ER  - 

@article{
author = "Šukalović, Vladimir and Ignjatović, Đurđica and Tovilović, Gordana and Andrić, Deana and Shakib, Kaveh and Kostić-Rajačić, Slađana and Šoškić, Vukić",
year = "2012",
abstract = "It is suggested that the ratio of dopamine D-2 to 5-hydroxytryptamine 5-HT1A activity is an important parameter that determines the efficiency of antipsychotic drugs. Here we present the synthesis of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas and their structure-activity relationship studies on dopamine D-2 and 5-hydrohytryptamine 5-HT1A receptors. It was shown that ligand selectivity and affinity strongly depends on their topology and the presence of a pyridyl group in the head of molecules. Molecular modeling studies using homology modeling and docking simulation revealed a rational explanation for the ligand behavior. The observed binding modes and receptor-ligand interactions provided us with a clue for optimizing the optimal selectivity towards 5-HT1A receptors. (C) 2012 Elsevier Ltd. All rights reserved.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic and Medicinal Chemistry Letters",
title = "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors",
volume = "22",
number = "12",
pages = "3967-3972",
doi = "10.1016/j.bmcl.2012.04.098"
}

Šukalović, V., Ignjatović, Đ., Tovilović, G., Andrić, D., Shakib, K., Kostić-Rajačić, S.,& Šoškić, V.. (2012). Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters
Pergamon-Elsevier Science Ltd, Oxford., 22(12), 3967-3972.
https://doi.org/10.1016/j.bmcl.2012.04.098

Šukalović V, Ignjatović Đ, Tovilović G, Andrić D, Shakib K, Kostić-Rajačić S, Šoškić V. Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors. in Bioorganic and Medicinal Chemistry Letters. 2012;22(12):3967-3972.
doi:10.1016/j.bmcl.2012.04.098 .

Šukalović, Vladimir, Ignjatović, Đurđica, Tovilović, Gordana, Andrić, Deana, Shakib, Kaveh, Kostić-Rajačić, Slađana, Šoškić, Vukić, "Interactions of N-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-2-aryl-2-yl-acetamides and 1-{[2-(4-phenyl-piperazin-1-yl)-ethyl]-phenyl}-3-aryl-2-yl-ureas with dopamine D-2 and 5-hydroxytryptamine 5HT(1A) receptors" in Bioorganic and Medicinal Chemistry Letters, 22, no. 12 (2012):3967-3972,
https://doi.org/10.1016/j.bmcl.2012.04.098 . .

TY  - DATA
AU  - Trmčić, Milena
AU  - Matović, Radomir
AU  - Tovilović, Gordana
AU  - Ristić, Biljana Z.
AU  - Trajković, Vladimir S.
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3673
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - Supplementary data for article:Trmčić, M.; Matović, R. V.; Tovilović, G.; Ristic, B. Z.; Trajković, V. S.; Ferjančić, Z.; Saičić, R. A Novel C,D-Spirolactone Analogue of Paclitaxel: Autophagy Instead of Apoptosis as a Previously Unknown Mechanism of Cytotoxic Action for Taxoids. Organic and Biomolecular Chemistry 2012, 10 (25), 4933–4942. https://doi.org/10.1039/c2ob25514f
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3673
ER  - 

@misc{
author = "Trmčić, Milena and Matović, Radomir and Tovilović, Gordana and Ristić, Biljana Z. and Trajković, Vladimir S. and Ferjančić, Zorana and Saičić, Radomir",
year = "2012",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "Supplementary data for article:Trmčić, M.; Matović, R. V.; Tovilović, G.; Ristic, B. Z.; Trajković, V. S.; Ferjančić, Z.; Saičić, R. A Novel C,D-Spirolactone Analogue of Paclitaxel: Autophagy Instead of Apoptosis as a Previously Unknown Mechanism of Cytotoxic Action for Taxoids. Organic and Biomolecular Chemistry 2012, 10 (25), 4933–4942. https://doi.org/10.1039/c2ob25514f",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3673"
}

Trmčić, M., Matović, R., Tovilović, G., Ristić, B. Z., Trajković, V. S., Ferjančić, Z.,& Saičić, R.. (2012). Supplementary data for article:Trmčić, M.; Matović, R. V.; Tovilović, G.; Ristic, B. Z.; Trajković, V. S.; Ferjančić, Z.; Saičić, R. A Novel C,D-Spirolactone Analogue of Paclitaxel: Autophagy Instead of Apoptosis as a Previously Unknown Mechanism of Cytotoxic Action for Taxoids. Organic and Biomolecular Chemistry 2012, 10 (25), 4933–4942. https://doi.org/10.1039/c2ob25514f. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3673

Trmčić M, Matović R, Tovilović G, Ristić BZ, Trajković VS, Ferjančić Z, Saičić R. Supplementary data for article:Trmčić, M.; Matović, R. V.; Tovilović, G.; Ristic, B. Z.; Trajković, V. S.; Ferjančić, Z.; Saičić, R. A Novel C,D-Spirolactone Analogue of Paclitaxel: Autophagy Instead of Apoptosis as a Previously Unknown Mechanism of Cytotoxic Action for Taxoids. Organic and Biomolecular Chemistry 2012, 10 (25), 4933–4942. https://doi.org/10.1039/c2ob25514f. in Organic and Biomolecular Chemistry. 2012;.
https://hdl.handle.net/21.15107/rcub_cherry_3673 .

Trmčić, Milena, Matović, Radomir, Tovilović, Gordana, Ristić, Biljana Z., Trajković, Vladimir S., Ferjančić, Zorana, Saičić, Radomir, "Supplementary data for article:Trmčić, M.; Matović, R. V.; Tovilović, G.; Ristic, B. Z.; Trajković, V. S.; Ferjančić, Z.; Saičić, R. A Novel C,D-Spirolactone Analogue of Paclitaxel: Autophagy Instead of Apoptosis as a Previously Unknown Mechanism of Cytotoxic Action for Taxoids. Organic and Biomolecular Chemistry 2012, 10 (25), 4933–4942. https://doi.org/10.1039/c2ob25514f" in Organic and Biomolecular Chemistry (2012),
https://hdl.handle.net/21.15107/rcub_cherry_3673 .

TY  - JOUR
AU  - Trmčić, Milena
AU  - Matović, Radomir
AU  - Tovilović, Gordana
AU  - Ristić, Biljana Z.
AU  - Trajković, Vladimir S.
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1304
AB  - The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic and Biomolecular Chemistry
T1  - A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids
VL  - 10
IS  - 25
SP  - 4933
EP  - 4942
DO  - 10.1039/c2ob25514f
ER  - 

@article{
author = "Trmčić, Milena and Matović, Radomir and Tovilović, Gordana and Ristić, Biljana Z. and Trajković, Vladimir S. and Ferjančić, Zorana and Saičić, Radomir",
year = "2012",
abstract = "The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic and Biomolecular Chemistry",
title = "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids",
volume = "10",
number = "25",
pages = "4933-4942",
doi = "10.1039/c2ob25514f"
}

Trmčić, M., Matović, R., Tovilović, G., Ristić, B. Z., Trajković, V. S., Ferjančić, Z.,& Saičić, R.. (2012). A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic and Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 10(25), 4933-4942.
https://doi.org/10.1039/c2ob25514f

Trmčić M, Matović R, Tovilović G, Ristić BZ, Trajković VS, Ferjančić Z, Saičić R. A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic and Biomolecular Chemistry. 2012;10(25):4933-4942.
doi:10.1039/c2ob25514f .

Trmčić, Milena, Matović, Radomir, Tovilović, Gordana, Ristić, Biljana Z., Trajković, Vladimir S., Ferjančić, Zorana, Saičić, Radomir, "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids" in Organic and Biomolecular Chemistry, 10, no. 25 (2012):4933-4942,
https://doi.org/10.1039/c2ob25514f . .

TY  - JOUR
AU  - Tomic, Mirko
AU  - Vaskovic, Djurdjica
AU  - Tovilović, Gordana
AU  - Andrić, Deana
AU  - Penjišević, Jelena
AU  - Kostić-Rajačić, Slađana
PY  - 2011
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1337
AB  - Five groups of previously synthesized and initially screened non-substituted and 4-halogenated arylpiperazin-1-yl-ethyl-benzimidazoles were estimated for their in-vitro binding affinities at the rat D-2, 5-HT2A, and alpha(1)-adrenergic receptors. Among all these compounds, 2-methoxyphenyl and 2-chlorophenyl piperazines demonstrate the highest affinities for the tested receptors. The effects of 4-halogenation of benzimidazoles reveal that substitution with brominemay greatly increase the affinity of the compounds for the studied receptors, while the effect of substitution with chlorine is less remarkable. Most of the tested components show 5-HT2A/D-2 pK(i) binding ratios slightly above or less than 1, while only 4-chloro-6-(2-{4-[3-(trifluoromethyl) phenyl]piperazin-1-yl}ethyl)-1H-benzimidazole expresses an appropriate higher binding ratio (1.14), which was indicated for atypical neuroleptics. This compound exhibits a non-cataleptic action in rats and prevents d-amphetamine-induced hyperlocomotion in mice, which suggest its atypical antipsychotic potency.
PB  - Wiley-Blackwell, Malden
T2  - Archiv der Pharmazie
T1  - Pharmacological Evaluation of Halogenated and Non-halogenated Arylpiperazin-1-yl-ethyl-benzimidazoles as D-2 and 5-HT2A Receptor Ligands
VL  - 344
IS  - 5
SP  - 287
EP  - 291
DO  - 10.1002/ardp.200900168
ER  - 

@article{
author = "Tomic, Mirko and Vaskovic, Djurdjica and Tovilović, Gordana and Andrić, Deana and Penjišević, Jelena and Kostić-Rajačić, Slađana",
year = "2011",
abstract = "Five groups of previously synthesized and initially screened non-substituted and 4-halogenated arylpiperazin-1-yl-ethyl-benzimidazoles were estimated for their in-vitro binding affinities at the rat D-2, 5-HT2A, and alpha(1)-adrenergic receptors. Among all these compounds, 2-methoxyphenyl and 2-chlorophenyl piperazines demonstrate the highest affinities for the tested receptors. The effects of 4-halogenation of benzimidazoles reveal that substitution with brominemay greatly increase the affinity of the compounds for the studied receptors, while the effect of substitution with chlorine is less remarkable. Most of the tested components show 5-HT2A/D-2 pK(i) binding ratios slightly above or less than 1, while only 4-chloro-6-(2-{4-[3-(trifluoromethyl) phenyl]piperazin-1-yl}ethyl)-1H-benzimidazole expresses an appropriate higher binding ratio (1.14), which was indicated for atypical neuroleptics. This compound exhibits a non-cataleptic action in rats and prevents d-amphetamine-induced hyperlocomotion in mice, which suggest its atypical antipsychotic potency.",
publisher = "Wiley-Blackwell, Malden",
journal = "Archiv der Pharmazie",
title = "Pharmacological Evaluation of Halogenated and Non-halogenated Arylpiperazin-1-yl-ethyl-benzimidazoles as D-2 and 5-HT2A Receptor Ligands",
volume = "344",
number = "5",
pages = "287-291",
doi = "10.1002/ardp.200900168"
}

Tomic, M., Vaskovic, D., Tovilović, G., Andrić, D., Penjišević, J.,& Kostić-Rajačić, S.. (2011). Pharmacological Evaluation of Halogenated and Non-halogenated Arylpiperazin-1-yl-ethyl-benzimidazoles as D-2 and 5-HT2A Receptor Ligands. in Archiv der Pharmazie
Wiley-Blackwell, Malden., 344(5), 287-291.
https://doi.org/10.1002/ardp.200900168

Tomic M, Vaskovic D, Tovilović G, Andrić D, Penjišević J, Kostić-Rajačić S. Pharmacological Evaluation of Halogenated and Non-halogenated Arylpiperazin-1-yl-ethyl-benzimidazoles as D-2 and 5-HT2A Receptor Ligands. in Archiv der Pharmazie. 2011;344(5):287-291.
doi:10.1002/ardp.200900168 .

Tomic, Mirko, Vaskovic, Djurdjica, Tovilović, Gordana, Andrić, Deana, Penjišević, Jelena, Kostić-Rajačić, Slađana, "Pharmacological Evaluation of Halogenated and Non-halogenated Arylpiperazin-1-yl-ethyl-benzimidazoles as D-2 and 5-HT2A Receptor Ligands" in Archiv der Pharmazie, 344, no. 5 (2011):287-291,
https://doi.org/10.1002/ardp.200900168 . .

TY  - JOUR
AU  - Andrić, Deana
AU  - Tovilović, Gordana
AU  - Roglić, Goran
AU  - Šoškić, Vukić
AU  - Tomic, Mirko
AU  - Kostić-Rajačić, Slađana
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/877
AB  - Eight new compounds with halogen atom introduced into the benzimidazole-2-thione dopaminergic pharmacophore of 5-[2-(4-arylpiperazin-1-yl)ethyl]-1,3-dihydro-2H-benzi -2-thiones with the arylpiperazine part of the molecule being selected according to known structure-affinity requirements, have been synthesized. All the new compounds were evaluated for the in vitro binding affinity at the dopamine (DA) D-1 and D-2 and serotonin 5-HT1A receptors by the competitive radioassays, performed on synaptosomal membranes prepared from fresh bovine caudate nuclei and hippocampi. All the new compounds were strong competitors for the binding of the radioligands to the D-2 and 5-HT1A receptors, with the most active of them having 34 and 170 time higher affinity than non-halogenated congeners in the D-2 DA receptor radioassays (compounds 9.1b and 9.2b, respectively). Divergently, these compounds were without significant affinities for the D-1 DA receptors.
AB  - Sintetisano je osam novih jedinjenja kod kojih je atom halogena uveden u benzimidazol-2-tionsku dopaminergičku farmakoforu 5-[2-(4-arilpiperazin-1-il)etil]-1,3-dihidro-2N-benzimidazol-2-tiona sa arilpiperazinskim delom molekula izabranim shodno pozna- tim zahtevima o odnosu strukture i reaktivnosti. Za sva novosintetisana jedinjenja je određen afinitet vezivanja za dopaminske (D1 i D2) i 5-NT1A receptore u in vitro eksperimentima kompeticije sa radioligandima. Kao izvor dopaminskih i 5-NT1A receptora su korištene sinaptozomalne membrane izolovane iz goveđeg nukleusa kaudatusa i hipokampusa. Sva novosintetisana jedinjenja pokazala su se kao jaki kompetitori [3H]spiperona i [3H]8-OH-DPAT, od kojih najaktivnija (9.1b i 9.2b) poseduju 34 i 170 puta veći afinitet ka D2 DA receptorima od polaznih, nehalogenovanih jedinjenja. Sa druge strane, ova jedinjenja ne poseduju značajan afinitet ka D1 dopaminskim receptorima. .
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation
T1  - 6-[2-(4-arilpiperazin-1-il)etil]-4-halo-1,3-dihidro-2h-benzimidazol-2-tioni - sinteza i farmakološko ispitivanje
VL  - 72
IS  - 8-9
SP  - 747
EP  - 755
DO  - 10.2298/JSC0709747A
ER  - 

@article{
author = "Andrić, Deana and Tovilović, Gordana and Roglić, Goran and Šoškić, Vukić and Tomic, Mirko and Kostić-Rajačić, Slađana",
year = "2007",
abstract = "Eight new compounds with halogen atom introduced into the benzimidazole-2-thione dopaminergic pharmacophore of 5-[2-(4-arylpiperazin-1-yl)ethyl]-1,3-dihydro-2H-benzi -2-thiones with the arylpiperazine part of the molecule being selected according to known structure-affinity requirements, have been synthesized. All the new compounds were evaluated for the in vitro binding affinity at the dopamine (DA) D-1 and D-2 and serotonin 5-HT1A receptors by the competitive radioassays, performed on synaptosomal membranes prepared from fresh bovine caudate nuclei and hippocampi. All the new compounds were strong competitors for the binding of the radioligands to the D-2 and 5-HT1A receptors, with the most active of them having 34 and 170 time higher affinity than non-halogenated congeners in the D-2 DA receptor radioassays (compounds 9.1b and 9.2b, respectively). Divergently, these compounds were without significant affinities for the D-1 DA receptors., Sintetisano je osam novih jedinjenja kod kojih je atom halogena uveden u benzimidazol-2-tionsku dopaminergičku farmakoforu 5-[2-(4-arilpiperazin-1-il)etil]-1,3-dihidro-2N-benzimidazol-2-tiona sa arilpiperazinskim delom molekula izabranim shodno pozna- tim zahtevima o odnosu strukture i reaktivnosti. Za sva novosintetisana jedinjenja je određen afinitet vezivanja za dopaminske (D1 i D2) i 5-NT1A receptore u in vitro eksperimentima kompeticije sa radioligandima. Kao izvor dopaminskih i 5-NT1A receptora su korištene sinaptozomalne membrane izolovane iz goveđeg nukleusa kaudatusa i hipokampusa. Sva novosintetisana jedinjenja pokazala su se kao jaki kompetitori [3H]spiperona i [3H]8-OH-DPAT, od kojih najaktivnija (9.1b i 9.2b) poseduju 34 i 170 puta veći afinitet ka D2 DA receptorima od polaznih, nehalogenovanih jedinjenja. Sa druge strane, ova jedinjenja ne poseduju značajan afinitet ka D1 dopaminskim receptorima. .",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation, 6-[2-(4-arilpiperazin-1-il)etil]-4-halo-1,3-dihidro-2h-benzimidazol-2-tioni - sinteza i farmakološko ispitivanje",
volume = "72",
number = "8-9",
pages = "747-755",
doi = "10.2298/JSC0709747A"
}

Andrić, D., Tovilović, G., Roglić, G., Šoškić, V., Tomic, M.,& Kostić-Rajačić, S.. (2007). 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(8-9), 747-755.
https://doi.org/10.2298/JSC0709747A

Andrić D, Tovilović G, Roglić G, Šoškić V, Tomic M, Kostić-Rajačić S. 6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation. in Journal of the Serbian Chemical Society. 2007;72(8-9):747-755.
doi:10.2298/JSC0709747A .

Andrić, Deana, Tovilović, Gordana, Roglić, Goran, Šoškić, Vukić, Tomic, Mirko, Kostić-Rajačić, Slađana, "6-[2-(4-Arylpiperazin-1-yl)ethyl]-4-halo-1,3-dihydro-2H-benzimidazole-2-thiones: synthesis and pharmacological evaluation" in Journal of the Serbian Chemical Society, 72, no. 8-9 (2007):747-755,
https://doi.org/10.2298/JSC0709747A . .

TY  - JOUR
AU  - Andrić, Deana
AU  - Tovilović, Gordana
AU  - Roglić, Goran
AU  - Vasković, Đurđica
AU  - Šoškić, Vukić
AU  - Tomic, Mirko
AU  - Kostić-Rajačić, Slađana
PY  - 2007
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/845
AB  - Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt  1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations.
AB  - Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives
T1  - Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina
VL  - 72
IS  - 5
SP  - 429
EP  - 435
DO  - 10.2298/JSC0705429A
ER  - 

@article{
author = "Andrić, Deana and Tovilović, Gordana and Roglić, Goran and Vasković, Đurđica and Šoškić, Vukić and Tomic, Mirko and Kostić-Rajačić, Slađana",
year = "2007",
abstract = "Six newly synthesized heterocyclic (2-nitroplienyl)piperazines. with a specific structure of the heteroaryl group, which mimics the catechol moiety of dopamine (benzimidazoles and substituted benzimidazoles), were evaluated for their binding affinity to rat dopamine (DA), serotonin (5-HT) and alpha I receptors. All compounds with a benzimidazole group had a 5-HT2A/D-2 receptors binding ratio characteristic for atypical neuroleptics ( gt  1, pK(i) values). Compound 7e, 4-bromo-6-{2-[4-(2-nitrophenyl)piperazin-1-yl]etliyl}-1H-benziniidazole, expressed higher affinities for all receptor classes than clozapine. Also, it exhibited the best characteristic for atypical neuroleptics and presents a compound with the best profile for further in vivo investigations., Sintetisano je šest heterocikličnih (2-nitrofenil)piperazina sa specifičnom heteroaril grupom, koja podražava kateholsku grupu dopamina (benzimidazoli i supstituisani benzimidazoli), i ispitan je njihov afinitet ka dopaminskim, serotoninskim i _1 receptorima. Sva jedinjenja sa benzimidazolskim grupama su pokazala 5-HT 1A/D2 odnos vezivanja karakterističan za atipične neuroleptike ( gt 1, pK i vrednosti). Jedinjenje 7c, 4-bromo-6-{2-_4-(2-nitrofenil)piperazin-1-il_etil}-1H-benzimidazol, pokazalo je izraženiji afinitet ka svim klasama receptora u poređenju sa klozapinom i takođe predstavlja jedinjenje sa najboljim karakteristikama za dalja in vivo istraživanja.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives, Sinteza i farmakološko ispitivanje novih derivata N-(2-nitrofenil) piperazina",
volume = "72",
number = "5",
pages = "429-435",
doi = "10.2298/JSC0705429A"
}

Andrić, D., Tovilović, G., Roglić, G., Vasković, Đ., Šoškić, V., Tomic, M.,& Kostić-Rajačić, S.. (2007). Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 72(5), 429-435.
https://doi.org/10.2298/JSC0705429A

Andrić D, Tovilović G, Roglić G, Vasković Đ, Šoškić V, Tomic M, Kostić-Rajačić S. Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives. in Journal of the Serbian Chemical Society. 2007;72(5):429-435.
doi:10.2298/JSC0705429A .

Andrić, Deana, Tovilović, Gordana, Roglić, Goran, Vasković, Đurđica, Šoškić, Vukić, Tomic, Mirko, Kostić-Rajačić, Slađana, "Synthesis and pharmacological evaluation of several N-(2-nitrophenyl)piperazine derivatives" in Journal of the Serbian Chemical Society, 72, no. 5 (2007):429-435,
https://doi.org/10.2298/JSC0705429A . .