Synthesis of chiral 2-(4-phenoxyphenylsulfonylmethyl)thiiranes as selective gelatinase inhibitors

Org Lett. 2005 Sep 29;7(20):4463-5. doi: 10.1021/ol0517269.

Abstract

[reactions: see text] Compound 1, 2-(4-phenoxyphenylsulfonylmethyl)thiirane, is a selective inhibitor of gelatinases, which is showing high promise in studies of animal models for cancer metastasis and stroke. The (R)-1 and (S)-1 enantiomers of compound 1 were each synthesized in this study and were shown to be equally active in inhibition of gelatinases.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Binding Sites
  • Kinetics
  • Matrix Metalloproteinase 2 / chemistry
  • Matrix Metalloproteinase 2 / metabolism
  • Matrix Metalloproteinase 9 / chemistry
  • Matrix Metalloproteinase 9 / metabolism
  • Matrix Metalloproteinase Inhibitors*
  • Methylation
  • Models, Molecular
  • Molecular Structure
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship
  • Sulfides / chemical synthesis
  • Sulfides / chemistry*
  • Sulfides / pharmacology*

Substances

  • Matrix Metalloproteinase Inhibitors
  • Protease Inhibitors
  • Sulfides
  • ethylene sulfide
  • Matrix Metalloproteinase 2
  • Matrix Metalloproteinase 9