Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 2: SAR of the acetylenic P1' group

Bioorg Med Chem Lett. 2002 Apr 22;12(8):1199-202. doi: 10.1016/s0960-894x(02)00136-1.

Abstract

The SAR of a series of potent sulfonamide hydroxamate TACE inhibitors bearing novel acetylenic P1' groups was explored. In particular, compound 4t bearing a butynyloxy P1' moiety has excellent in vitro potency against isolated TACE enzyme and in cells, good selectivity over MMP-1 and oral activity in an in vivo model of TNF-alpha production.

MeSH terms

  • ADAM Proteins
  • ADAM17 Protein
  • Acetylene / chemistry*
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / pharmacology*
  • Hydroxamic Acids / chemistry*
  • Hydroxamic Acids / pharmacology*
  • Metalloendopeptidases / antagonists & inhibitors*
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis*
  • Sulfonamides / pharmacology*
  • ortho-Aminobenzoates / chemistry*
  • ortho-Aminobenzoates / pharmacology*

Substances

  • Enzyme Inhibitors
  • Hydroxamic Acids
  • Sulfonamides
  • ortho-Aminobenzoates
  • ADAM Proteins
  • Metalloendopeptidases
  • ADAM17 Protein
  • Acetylene