Structure and property based design of factor Xa inhibitors: pyrrolidin-2-ones with monoaryl P4 motifs

Bioorg Med Chem Lett. 2010 Jan 15;20(2):618-22. doi: 10.1016/j.bmcl.2009.11.077. Epub 2009 Nov 20.

Abstract

Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa inhibitors, incorporating neutral and basic monoaryl P4 groups, ultimately producing potent inhibitors with effective levels of anticoagulant activity and extended oral pharmacokinetic profiles. However, time dependant inhibition of Cytochrome P450 3A4 was a particular issue with this series.

MeSH terms

  • Anticoagulants / chemical synthesis
  • Anticoagulants / chemistry*
  • Anticoagulants / pharmacology
  • Binding Sites
  • Computer Simulation
  • Crystallography, X-Ray
  • Drug Design
  • Factor X / antagonists & inhibitors*
  • Factor X / metabolism
  • Pyrrolidinones / chemical synthesis
  • Pyrrolidinones / chemistry*
  • Pyrrolidinones / pharmacology
  • Structure-Activity Relationship

Substances

  • Anticoagulants
  • Pyrrolidinones
  • Factor X

Associated data

  • PDB/2WYG
  • PDB/2WYJ