beta-N-Biaryl ether sulfonamide hydroxamates as potent gelatinase inhibitors: part 1. Design, synthesis, and lead identification

Bioorg Med Chem Lett. 2008 Feb 1;18(3):1135-9. doi: 10.1016/j.bmcl.2007.11.119. Epub 2007 Dec 5.

Abstract

A new series of beta-N-biaryl ether sulfonamide hydroxamates as novel gelatinase inhibitors is described. These compounds exhibit good potency for MMP-2 and MMP-9 without inhibiting MMP-1. The structure-activity relationships (SAR) reveal the biaryl ether type P1' moiety together with methanesulfonamide is the optimal combination that provides inhibitory activity of MMP-9 in the single-digit nanomolar range.

MeSH terms

  • Animals
  • Drug Design
  • Gelatinases / antagonists & inhibitors*
  • Humans
  • Hydroxamic Acids / chemical synthesis*
  • Hydroxamic Acids / chemistry
  • Hydroxamic Acids / pharmacology*
  • Matrix Metalloproteinase Inhibitors*
  • Microsomes, Liver / drug effects
  • Molecular Structure
  • Pyrazines / chemical synthesis*
  • Pyrazines / chemistry
  • Pyrazines / pharmacology*
  • Rats
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology

Substances

  • CGS 27023A
  • Hydroxamic Acids
  • Matrix Metalloproteinase Inhibitors
  • Pyrazines
  • Sulfonamides
  • Gelatinases