2 beta-substituted analogues of cocaine. Synthesis and inhibition of binding to the cocaine receptor

J Med Chem. 1992 Jan;35(1):135-40. doi: 10.1021/jm00079a017.

Abstract

The potencies of a series of 2 beta-substituted cocaine analogues to displace [3H]-3 beta-(p-fluorophenyl)tropane-2 beta-carboxylic acid methyl ester binding in rat striatal membranes demonstrate the requirement for a 2 beta-substituent with two hydrogen-bond acceptors. The insensitivity of the ester moiety to steric and electronic factors suggests its modification to provide site-specific irreversible ligands.

Publication types

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

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / chemistry
  • Analgesics / pharmacology
  • Animals
  • Binding Sites
  • Carrier Proteins*
  • Cocaine / analogs & derivatives*
  • Cocaine / chemistry
  • Cocaine / pharmacology
  • Corpus Striatum / drug effects
  • Corpus Striatum / metabolism
  • Male
  • Rats
  • Rats, Inbred Strains
  • Receptors, Drug / drug effects*
  • Receptors, Drug / metabolism
  • Structure-Activity Relationship

Substances

  • Analgesics
  • Carrier Proteins
  • Receptors, Drug
  • cocaine receptor
  • Cocaine