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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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, 708-717Publisher:
- Wiley-V C H Verlag Gmbh, Weinheim
Projects:
DOI: 10.1002/ardp.201300189
ISSN: 0365-6233
PubMed: 24105736