Synthesis, phencyclidine-like pharmacology, and antiischemic potential of meta-substituted 1-(1-phenylcyclohexyl)-1,2,3,6-tetrahydropyridines

J Med Chem. 1990 Aug;33(8):2211-5. doi: 10.1021/jm00170a027.

Abstract

A series of 1-[1-arylcyclohexyl]-1,2,3,6-tetrahydropyridines were prepared by the reaction between 1-(1-cyanocyclohexyl)-1,2,3,6-tetrahydropyridine (1) and an appropriately substituted Grignard reagent. The resulting compounds were tested for their phencyclidine binding site affinities. Selected compounds were then tested for their ability to produce ketamine appropriate responding in monkeys and/or to show neuroprotective effects in a baby rat hypoxia/ischemia model. While it was found that binding site affinity correlated well with discriminative stimulus effects, it was found to be a poor indicator of neuroprotective efficacy within this series.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Animals
  • Animals, Newborn
  • Binding Sites
  • Brain / drug effects
  • Brain / metabolism
  • Chemical Phenomena
  • Chemistry
  • Discrimination, Psychological / drug effects
  • Hypoxia / prevention & control
  • Ischemia / prevention & control*
  • Ketamine
  • Macaca mulatta
  • Molecular Structure
  • Phencyclidine / analogs & derivatives*
  • Phencyclidine / metabolism
  • Phencyclidine / pharmacology
  • Pyridines / chemical synthesis*
  • Pyridines / metabolism
  • Pyridines / pharmacology
  • Rats
  • Structure-Activity Relationship

Substances

  • Pyridines
  • Ketamine
  • tenocyclidine
  • Phencyclidine