alpha-Ketocarboxylic acid-based inhibitors of protein tyrosine phosphatases

Bioorg Med Chem Lett. 2001 Jul 23;11(14):1935-8. doi: 10.1016/s0960-894x(01)00325-0.

Abstract

A series of aryl alpha-ketocarboxylic acids was synthesized and investigated as inhibitors for the protein tyrosine phosphatase from Yersinia enterocolitica. IC(50) values for these compounds range from 79 to 2700 microM. Larger aromatic groups, and aromatic groups with high electron density, lead to more potent inhibitors. In general, the related aryl alpha-hydroxycarboxylic acids show lower activity.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Binding Sites / physiology
  • Carboxylic Acids / chemical synthesis
  • Carboxylic Acids / pharmacology
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Inhibitory Concentration 50
  • Ketones / chemistry
  • Oxidation-Reduction
  • Phosphotyrosine / chemistry
  • Protein Tyrosine Phosphatases / antagonists & inhibitors*
  • Yersinia enterocolitica / enzymology*

Substances

  • Carboxylic Acids
  • Enzyme Inhibitors
  • Ketones
  • Phosphotyrosine
  • Protein Tyrosine Phosphatases