Abstract
(±)-Trans-Ph/Et and (±)-cis-Ph/Et 1-(2-ethyl-1-phenylcyclohexyl)piperidine were synthesized from 2-ethylcyclohexanone. In contrast to the corresponding trans-substituted 2-methyl compound which is 5x more potent than PCP, the trans-2-ethyl derivative has a 75x lower affinity for the PCP binding site. The cis-2-ethyl isomer is inactive like the cis-2-methyl derivative. (±)-1-(1- Phenylcyclohexyl)-2-methylpiperidine is almost as active as the parent PCP. Reduction of the aromatic ring or quaternization of the piperidine in PCP reduces the affinity for the PCP site.
Keywords: Phencyclidine, Conformations, NMDA receptor, PCP binding site, Bruylants reaction, Ritter reaction
Letters in Drug Design & Discovery
Title: Synthesis and Preliminary Biochemical Evaluation of Novel Derivatives of PCP
Volume: 7 Issue: 2
Author(s): Joannes T.M. Linders, David C. Furlano, Mariena V. Mattson, Arthur E. Jacobson and Kenner C. Rice
Affiliation:
Keywords: Phencyclidine, Conformations, NMDA receptor, PCP binding site, Bruylants reaction, Ritter reaction
Abstract: (±)-Trans-Ph/Et and (±)-cis-Ph/Et 1-(2-ethyl-1-phenylcyclohexyl)piperidine were synthesized from 2-ethylcyclohexanone. In contrast to the corresponding trans-substituted 2-methyl compound which is 5x more potent than PCP, the trans-2-ethyl derivative has a 75x lower affinity for the PCP binding site. The cis-2-ethyl isomer is inactive like the cis-2-methyl derivative. (±)-1-(1- Phenylcyclohexyl)-2-methylpiperidine is almost as active as the parent PCP. Reduction of the aromatic ring or quaternization of the piperidine in PCP reduces the affinity for the PCP site.
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Cite this article as:
Linders T.M. Joannes, Furlano C. David, Mattson V. Mariena, Jacobson E. Arthur and Rice C. Kenner, Synthesis and Preliminary Biochemical Evaluation of Novel Derivatives of PCP, Letters in Drug Design & Discovery 2010; 7 (2) . https://dx.doi.org/10.2174/157018010790225813
DOI https://dx.doi.org/10.2174/157018010790225813 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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