Synthesis and analgesic activity of pemedolac (cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]ind ole-1- acetic acid)

J Med Chem. 1988 Jun;31(6):1244-50. doi: 10.1021/jm00401a029.

Abstract

The synthesis of cis-1-ethyl-1,3,4,9-tetrahydro-4-(phenylmethyl)pyrano[3,4-b]indole -1-acetic acid, pemedolac (USAN), is described. This compound has been found to be a potent analgesic agent in primary screening. Pemedolac has been resolved and the active (+)-enantiomer assigned a 1S,4R absolute configuration on the basis of a crystallographic analysis of its (S)-(-)-borneol ester.

MeSH terms

  • Acetates / chemical synthesis*
  • Acetates / pharmacology
  • Analgesics / chemical synthesis*
  • Analgesics / pharmacology
  • Animals
  • Anti-Inflammatory Agents / pharmacology
  • Indoleacetic Acids*
  • Male
  • Mice
  • Molecular Conformation
  • Rats
  • Rats, Inbred Strains
  • Structure-Activity Relationship

Substances

  • Acetates
  • Analgesics
  • Anti-Inflammatory Agents
  • Indoleacetic Acids
  • pemedolac