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
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2013
Authors
Šukalović, Vladimir
Bogdan, Anca Elena
Tovilović, Gordana

Ignjatović, Đurđica S.

Andrić, Deana

Kostić Rajačić, Slađana

Šoškić, Vukić

Article (Published version)

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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.
Keywords:
Arylpiperazine / Dopamine receptors / Serotonin receptorsSource:
Archiv der Pharmazie, 2013, 346, 10, 708-717Publisher:
- Wiley-V C H Verlag Gmbh, Weinheim
Projects:
DOI: 10.1002/ardp.201300189
ISSN: 0365-6233
PubMed: 24105736
WoS: 000325497500002
Scopus: 2-s2.0-84885595739
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IHTMTY - JOUR AU - Šukalović, Vladimir AU - Bogdan, Anca Elena AU - Tovilović, Gordana AU - Ignjatović, Đurđica S. AU - Andrić, Deana AU - Kostić Rajačić, Slađana AU - Šoškić, Vukić PY - 2013 UR - http://cer.ihtm.bg.ac.rs/handle/123456789/1193 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 S. and Andrić, Deana and Kostić Rajačić, Slađana and Šoškić, Vukić", year = "2013", url = "http://cer.ihtm.bg.ac.rs/handle/123456789/1193", 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 AE, Tovilović G, Ignjatović ĐS, 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
Šukalović, V., Bogdan, A. E., Tovilović, G., Ignjatović, Đ. S., 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. Archiv der PharmazieWiley-V C H Verlag Gmbh, Weinheim., 346(10), 708-717. https://doi.org/10.1002/ardp.201300189
Šukalović Vladimir, Bogdan Anca Elena, Tovilović Gordana, Ignjatović Đurđica S., 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" 346, no. 10 (2013):708-717, https://doi.org/10.1002/ardp.201300189 .