Synthesis and Preliminary Biochemical Evaluation of Novel Derivatives of PCP

Author(s): Joannes T.M. Linders, David C. Furlano, Mariena V. Mattson, Arthur E. Jacobson, Kenner C. Rice

Journal Name: Letters in Drug Design & Discovery

Volume 7 , Issue 2 , 2010

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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

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Article Details

VOLUME: 7
ISSUE: 2
Year: 2010
Page: [79 - 87]
Pages: 9
DOI: 10.2174/157018010790225813
Price: $65

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