Synthesis and pharmacological evaluation of peptide-mimetic protease-activated receptor-1 antagonists containing novel heterocyclic scaffolds

Bioorg Med Chem. 2008 Jun 1;16(11):6009-20. doi: 10.1016/j.bmc.2008.04.059. Epub 2008 Apr 26.

Abstract

Protease-activated receptor-1 (PAR-1) is a G-coupled receptor activated by alpha-thrombin and other proteases. In this paper we describe the synthesis and the pharmacological evaluation of novel peptide-mimetic antagonists (compounds 1-16) characterized by the presence of new heterocyclic nuclei such as 2-methyl-indole (5- and 6-substituted) and 1,4-benzodiazepine moiety. The new derivatives, tested in order to evaluate their antagonist potency by using human platelet aggregation induced by PAR-1AP, resulted in some cases (compounds 1 and 4) more potent than the reference. The compounds, tested on aortic rings, confirmed the results obtained in the aggregation assay.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aorta, Thoracic / drug effects
  • Aorta, Thoracic / physiology
  • Heterocyclic Compounds / chemical synthesis*
  • Heterocyclic Compounds / pharmacology
  • Humans
  • Indoles / chemical synthesis
  • Indoles / pharmacology
  • Male
  • Molecular Mimicry*
  • Peptides / chemical synthesis*
  • Peptides / pharmacology
  • Platelet Aggregation / drug effects
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / pharmacology
  • Rats
  • Rats, Wistar
  • Receptor, PAR-1 / antagonists & inhibitors*
  • Vasoconstriction / drug effects

Substances

  • Heterocyclic Compounds
  • Indoles
  • Peptides
  • Protease Inhibitors
  • Receptor, PAR-1