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
2013
Authors:
Šukalović, VladimirBogdan, Anca Elena
Tovilović-Kovačević, Gordana
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Ignjatović, Đurđica
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Andrić, Deana
Kostić-Rajačić, Slađana
Šoškić, Vukić
Document Type:
Article (Published version)
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© 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Metadata
Show full item recordAbstract:
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, 708-717Funding / projects:
- Structure-activity relationship of newly synthesized biological active compound (RS-MESTD-Basic Research (BR or ON)-172032)
DOI: 10.1002/ardp.201300189
ISSN: 0365-6233
PubMed: 24105736