Synthesis and structure-activity relationships in a series of ethenesulfonamide derivatives, a novel class of endothelin receptor antagonists

Chem Pharm Bull (Tokyo). 2001 Dec;49(12):1593-603. doi: 10.1248/cpb.49.1593.

Abstract

In the previous paper, we described a series of the 2-arylethenesulfonamide derivatives, a novel class of ETA-selective endothelin (ET) receptor antagonists, including the compounds 1a, b. Compound 1a showed excellent oral antagonistic activities and pharmacokinetic profiles, and the monopotassium salt of 1 (YM-598 monopotassium) is in clinical trials. In this paper, we wish to report the investigation of the further details of structure-activity relationships (SARs) of the 2-phenylethenesulfonamide region in 1a. It was found that methyl substitutions at the 2-, 4- and 6-positions of the phenyl group in 1a led to the discovery of the ET(A)/ET(B) mixed antagonist (6s) with an IC50 of 2.2 nM for the ET(A) receptor. We also found that introduction of an ethyl group to the 1-position of the ethenyl group in 1a gave the ET(A) selective antagonist (6u) with an oral endothelin antagonistic activity in rats.

MeSH terms

  • Animals
  • Blood Pressure / drug effects
  • COS Cells
  • Cloning, Molecular
  • Decerebrate State
  • Endothelin Receptor Antagonists*
  • Endothelin-1
  • Endothelins / antagonists & inhibitors
  • Magnetic Resonance Spectroscopy
  • Male
  • Protein Precursors / antagonists & inhibitors
  • Rats
  • Rats, Wistar
  • Receptor, Endothelin A
  • Receptor, Endothelin B
  • Spectrometry, Mass, Fast Atom Bombardment
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology

Substances

  • Endothelin Receptor Antagonists
  • Endothelin-1
  • Endothelins
  • Protein Precursors
  • Receptor, Endothelin A
  • Receptor, Endothelin B
  • Sulfonamides