Potent P2Y1 urea antagonists bearing various cyclic amine scaffolds

Bioorg Med Chem Lett. 2013 Dec 15;23(24):6825-8. doi: 10.1016/j.bmcl.2013.10.009. Epub 2013 Oct 11.

Abstract

A number of new amine scaffolds with good inhibitory activity in the ADP-induced platelet aggregation assay have been found to be potent antagonists of the P2Y1 receptor. SAR optimization led to the identification of isoindoline 3c and piperidine 4a which showed good in vitro binding and functional activities, as well as improved aqueous solubility. Among them, the piperidine 4a showed the best overall profile with favorable PK parameters.

Keywords: Isoindolines; P2Y(1) antagonists; Piperidines; Purinergic receptors; Tetrahydroisoquinolines.

MeSH terms

  • Adenosine Diphosphate / pharmacology
  • Amines / chemical synthesis
  • Amines / chemistry*
  • Amines / pharmacokinetics
  • Animals
  • Blood Platelets / drug effects
  • Blood Platelets / metabolism
  • Half-Life
  • Humans
  • Microsomes, Liver / metabolism
  • Piperidines / chemistry
  • Platelet Aggregation Inhibitors / chemical synthesis
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / pharmacokinetics
  • Protein Binding
  • Purinergic P2Y Receptor Agonists / chemical synthesis
  • Purinergic P2Y Receptor Agonists / chemistry*
  • Purinergic P2Y Receptor Agonists / pharmacokinetics
  • Rats
  • Receptors, Purinergic P2Y1 / chemistry*
  • Receptors, Purinergic P2Y1 / metabolism
  • Structure-Activity Relationship
  • Urea / analogs & derivatives*
  • Urea / chemical synthesis
  • Urea / pharmacokinetics

Substances

  • Amines
  • Piperidines
  • Platelet Aggregation Inhibitors
  • Purinergic P2Y Receptor Agonists
  • Receptors, Purinergic P2Y1
  • Adenosine Diphosphate
  • piperidine
  • Urea