Chiral synthesis and pharmacological evaluation of the enantiomers of SM32, a new analgesic and cognition-enhancing agent

Chirality. 1996;8(8):579-84. doi: 10.1002/(SICI)1520-636X(1996)8:8<579::AID-CHIR7>3.0.CO;2-4.

Abstract

The enantiomers of 3-alpha-tropyl 2-(phenylthio)butyrate (SM32, 1) were prepared by chiral synthesis and tested for analgesic, cognition-enhancing, and ACh-releasing properties. They show enantioselectivity in some of the tests, the eutomer being related in configuration to R-(+)-hyoscyamine.

MeSH terms

  • Acetylcholine / metabolism
  • Analgesics / chemical synthesis*
  • Analgesics / chemistry
  • Analgesics / pharmacology*
  • Animals
  • Atropine / chemistry
  • Avoidance Learning / drug effects
  • Behavior, Animal / drug effects
  • Cognition / drug effects*
  • Male
  • Mice
  • Rats
  • Rats, Wistar
  • Stereoisomerism
  • Tropanes / chemical synthesis*
  • Tropanes / chemistry
  • Tropanes / pharmacology*

Substances

  • 3-alpha-tropyl-2-(phenylthio)butyrate
  • Analgesics
  • Tropanes
  • Atropine
  • Acetylcholine