Synthesis and Chemical Resolution of a Novel Class of Rigid 1-(1-Phenylcyclohexyl)-iperidine(PCP) Analogues

Alan P. Kozikowski, Yuan Ping Pang

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

A novel class of conformationally rigidified phencyclidine (1-(1-phenylcyclohexyl)piperidine; PCP) analogues-4a-amino-1,4,4a,9a-tetrahydrofluorenes 1, 2, 5, 6 and 4a-amino-1,2,3,4,4a,9a-hexahydrofluorenes 3, 4, 7, 8-has been prepared through a Diels-Alder approach and resolved by aid of (+)- A nd (-)-tartaric acid. One member of this series, the (4aR, 9aS)-4a-amino derivative 3, was found to exhibit a high affinity (IC 50 = 19 nm) for the PCP recognition site in the brain, thus allowing a more rigorous assignment of the conformation of PCP relevant to binding at these sites.

Original languageEnglish (US)
Pages (from-to)58-63
Number of pages6
JournalSynlett
Volume1990
Issue number1
DOIs
StatePublished - Jan 1990

ASJC Scopus subject areas

  • Organic Chemistry

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