PMID: 9436302Jan 22, 1998Paper

Structure and serotonin 5-HT2C receptor activity of ortho- and meta-substituted phenylpiperazines

Acta Crystallographica. Section B, Structural Science
M L VerdonkJ Kelder

Abstract

The structural characteristics of ortho- and meta-substituted phenylpiperazines have been investigated in order to understand their actions at the serotonin 5-HT2C receptor. The crystal structures of the 4-methylated analogues of two phenylpiperazines that are already known as 5-HT2C ligands, 1-(1-naphthyl)-4-methylpiperazine (1NMP) and 1-[(3-trifluoromethyl)phenyl]-4-methylpiperazine (TFMPMP), and those of two novel 5-HT2C ligands, 1-(2-methoxyphenyl)piperazine (oMPP) and 1-(3-methoxyphenyl)piperazine (mMPP), are determined. Molecular mechanics calculations are performed to calculate the energy profiles of six phenylpiperazines for rotation about the central phenyl-nitrogen bond. The activities of several phenylpiperazines, in combination with their crystal structures and conformational characteristics, lead to the hypothesis that the conformation for which the piperazine ring and the phenyl ring are approximately co-planar should be the 5-HT2C receptor 'activating' conformation. This hypothesis is then used to predict the activities of the two novel 5-HT2C ligands oMPP and mMPP. oMPP is predicted to be an antagonist at this receptor, whereas mMPP is predicted to be an agonist. As this prediction was confirmed by in vitro and ...Continue Reading

Citations

Apr 28, 2011·Acta Crystallographica. Section E, Structure Reports Online·Grzegorz DutkiewiczMaciej Kubicki
Jul 9, 2013·Journal of Pharmaceutical and Biomedical Analysis·Jitka SirokáMiroslav Polášek
Oct 23, 2019·Acta Crystallographica. Section E, Crystallographic Communications·Haruvegowda Kiran KumarChristopher Glidewell
Nov 20, 2020·Acta Crystallographica. Section E, Crystallographic Communications·Chayanna Harish ChinthalChristopher Glidewell

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