Discovery of novel spirocyclopropyl hydroxamate and carboxylate compounds as TACE inhibitors

Bioorg Med Chem Lett. 2009 Jan 1;19(1):54-7. doi: 10.1016/j.bmcl.2008.11.034. Epub 2008 Nov 14.

Abstract

We have discovered nanomolar inhibitors of TNF-alpha convertase (TACE) comprised of a novel spirocyclic scaffold and either a carboxylate or hydroxamate zinc binding moiety. X-ray crystal structures and computer models of selected compounds binding to TACE explain the observed SAR. We report the first TACE X-ray crystal structure for an inhibitor with a carboxylate zinc ligand.

MeSH terms

  • ADAM Proteins / antagonists & inhibitors*
  • ADAM17 Protein
  • Carboxylic Acids / chemistry*
  • Carboxylic Acids / pharmacology
  • Computer Simulation
  • Crystallography, X-Ray
  • Hydroxamic Acids / chemistry*
  • Hydroxamic Acids / pharmacology
  • Ligands
  • Models, Molecular
  • Protein Binding
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology
  • Structure-Activity Relationship
  • Zinc

Substances

  • Carboxylic Acids
  • Hydroxamic Acids
  • Ligands
  • Spiro Compounds
  • ADAM Proteins
  • ADAM17 Protein
  • Zinc