Imidodisulfamides. 1. A novel class of antagonists of slow-reacting substance of anaphylaxis

J Med Chem. 1982 Aug;25(8):947-52. doi: 10.1021/jm00350a012.

Abstract

A series of N',N"-bis(aryl)- and N',N"-(aralkyl)imidodisulfamides was prepared and evaluated as antagonists of slow-reacting substance of anaphylaxis (SRS-A) induced contractions of isolated guinea pig ileum. Some of these compounds, notably N',N"-bis(4-phenylbutyl)-, N',N"-bis[2-(4-chlorophenyl)ethyl]-, and N',N"-bis[2-(4-bromophenyl)ethyl]imidodisulfamides (16, 22, and 26), were moderately potent and selective antagonists of SRS-A. The influence of lipophilic (pi) and electronic (sigma) factors on SRS-A antagonist activity appears to be of considerable importance to the derivation of potent and selective SRS-A antagonists.

MeSH terms

  • Animals
  • Chemical Phenomena
  • Chemistry
  • Guinea Pigs
  • Imides / chemical synthesis*
  • Imides / pharmacology
  • In Vitro Techniques
  • Male
  • Molecular Conformation
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • SRS-A / antagonists & inhibitors*
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology

Substances

  • Imides
  • SRS-A
  • Sulfonamides