Synthesis of a tetronic acid library focused on inhibitors of tyrosine and dual-specificity protein phosphatases and its evaluation regarding VHR and cdc25B inhibition

J Med Chem. 2001 Sep 27;44(20):3216-22. doi: 10.1021/jm0100741.

Abstract

Selective inhibitors of protein tyrosine phosphatases (PTPs) and dual-specificity phosphatases (DSPs) are expected to be useful tools for clarifying the biological functions of the PTPs themselves and also to be candidates for novel therapeutics. We planned a library approach for the identification of PTP/DSP inhibitors in which 3-acyltetronic acid is used as a "core" phosphate mimic. A series of novel tetronic acid derivatives were synthesized and evaluated as inhibitors of the dual-specificity protein phosphatases VHR and cdc25B. Several compounds are found to be potent inhibitors of cdc25B, which is a key enzyme for cell-cycle progression. The promising results described herein strongly indicated that this tetronic acid library is potent as a library focused on the PTP/DSP-selective inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Cycle Proteins / antagonists & inhibitors*
  • Cell Cycle Proteins / chemistry
  • Cell Cycle Proteins / metabolism
  • Combinatorial Chemistry Techniques
  • Dual Specificity Phosphatase 3
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Escherichia coli / metabolism
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Models, Molecular
  • Protein Binding
  • Protein Tyrosine Phosphatases / antagonists & inhibitors*
  • Protein Tyrosine Phosphatases / chemistry
  • Protein Tyrosine Phosphatases / metabolism
  • Structure-Activity Relationship
  • cdc25 Phosphatases / antagonists & inhibitors*
  • cdc25 Phosphatases / chemistry
  • cdc25 Phosphatases / metabolism

Substances

  • Cell Cycle Proteins
  • Enzyme Inhibitors
  • Furans
  • Dual Specificity Phosphatase 3
  • Protein Tyrosine Phosphatases
  • cdc25 Phosphatases
  • tetronic acid