Design, synthesis, and thrombin-inhibitory activity of pyridin-2-ones as P2/P3 core motifs

Bioorg Med Chem Lett. 2008 Mar 15;18(6):1972-6. doi: 10.1016/j.bmcl.2008.01.122. Epub 2008 Feb 7.

Abstract

Guided by available X-ray crystal structure data on the serine protease thrombin, a series of pyridin-2-one derivatives were designed and synthesized having diverse functionality at the P(1) and P(3) sites. Potent in vitro activity against thrombin, with excellent selectivity over trypsin was found for selected analogues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Crystallography, X-Ray
  • Drug Design*
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Protein Binding
  • Protein Structure, Tertiary
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry
  • Pyridones / pharmacology*
  • Structure-Activity Relationship
  • Sulfonamides / chemistry
  • Thrombin / antagonists & inhibitors*
  • Thrombin / metabolism
  • Trypsin / chemistry
  • Trypsin / metabolism

Substances

  • Amines
  • Pyridones
  • Sulfonamides
  • 2-hydroxypyridine
  • Trypsin
  • Thrombin