Benzylamine-based selective and orally bioavailable inhibitors of thrombin

Bioorg Med Chem Lett. 1998 Sep 22;8(18):2563-8. doi: 10.1016/s0960-894x(98)00456-9.

Abstract

A series of p-aminomethylphenylalanine derivatives were investigated as novel thrombin inhibitors. This study led to potent inhibitors of thrombin (Ki up to 3.3 nM) that are trypsin-selective, highly orally bioavailable in rats, and highly permeable across Caco-2 cells. The P1 benzylamine binding mode in the thrombin active site was identified by X-ray crystallographic analysis.

MeSH terms

  • Animals
  • Benzylamines / chemistry*
  • Biological Availability
  • Caco-2 Cells
  • Crystallography, X-Ray
  • Humans
  • Kinetics
  • Models, Molecular
  • Rats
  • Serine Proteinase Inhibitors / chemical synthesis
  • Serine Proteinase Inhibitors / pharmacokinetics*
  • Serine Proteinase Inhibitors / pharmacology
  • Thrombin / antagonists & inhibitors*

Substances

  • Benzylamines
  • Serine Proteinase Inhibitors
  • benzylamine
  • Thrombin