Solid-phase synthesis of alpha-substituted 3-bisarylthio N-hydroxy propionamides as specific MMP inhibitors

Bioorg Med Chem. 2002 Mar;10(3):531-44. doi: 10.1016/s0968-0896(01)00311-x.

Abstract

A novel series of potent and specific MMP-2,3,9,13 inhibitors has been obtained by modulation on solid phase by alpha and aryl substitutions on 3-arylthio-N-hydroxy-propionamides starting from itaconic acid.

MeSH terms

  • Amides / chemical synthesis*
  • Amides / pharmacology
  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology
  • Cartilage, Articular / drug effects
  • Cartilage, Articular / metabolism
  • Combinatorial Chemistry Techniques*
  • Enzyme Inhibitors / chemical synthesis
  • Enzyme Inhibitors / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Matrix Metalloproteinase Inhibitors*
  • Melanoma / drug therapy
  • Mice
  • Neoplasm Metastasis / drug therapy
  • Proteoglycans / drug effects
  • Proteoglycans / metabolism
  • Rabbits
  • Structure-Activity Relationship

Substances

  • Amides
  • Antineoplastic Agents
  • Enzyme Inhibitors
  • Matrix Metalloproteinase Inhibitors
  • Proteoglycans
  • propionamide