Discovery and structure-activity relationships of sulfonamide ETA-selective antagonists

J Med Chem. 1995 Apr 14;38(8):1344-54. doi: 10.1021/jm00008a013.

Abstract

Random screening of compounds in an ETA receptor binding assay led to the discovery of a class of benzenesulfonamide ligands. Optimization led to the development of 5-amino-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamides which were functional antagonists. Structural features which were important to activity included a 1,5-substitution pattern on the naphthalene ring; a sulfonamide NH with a pK value < 7; an amine, preferably with alkyl substituents, at the 5-position; and methyl groups on both the 3- and 4-positions of the isoxazole.

MeSH terms

  • Animals
  • Benzenesulfonamides
  • Carotid Arteries / drug effects
  • Carotid Arteries / metabolism
  • Cell Line
  • Endothelin Receptor Antagonists*
  • In Vitro Techniques
  • Muscle, Smooth, Vascular / drug effects
  • Muscle, Smooth, Vascular / metabolism
  • Rabbits
  • Radioligand Assay
  • Rats
  • Receptor, Endothelin A
  • Structure-Activity Relationship
  • Sulfonamides / chemistry*
  • Sulfonamides / metabolism
  • Sulfonamides / pharmacology*

Substances

  • Endothelin Receptor Antagonists
  • Receptor, Endothelin A
  • Sulfonamides
  • naphthalenesulfonamide