Synthesis and in vitro antiplatelet activity of new 4-(1-piperazinyl)coumarin derivatives. Human platelet phosphodiesterase 3 inhibitory properties of the two most effective compounds described and molecular modeling study on their interactions with phosphodiesterase 3A catalytic site

J Med Chem. 2007 Jun 14;50(12):2886-95. doi: 10.1021/jm0611511. Epub 2007 May 15.

Abstract

The synthesis and in vitro antiplatelet activity significant data of coumarin derivatives 5i-x and quinolin-2(1H)-one derivatives 22a,b, as well as the corresponding structure-activity relationships are described. The recently reported 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin 5f and its potent 7-(2-morpholinoethoxy)-substituted new analogue 5u were notably more effective inhibitors of pure human platelet PDE3 than milrinone and cilostazol: these data were related, through a molecular modeling study, with the molecular interactions of the four compounds with the human PDE3A catalytic site.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
  • 3',5'-Cyclic-AMP Phosphodiesterases / blood
  • 3',5'-Cyclic-AMP Phosphodiesterases / chemistry
  • Catalytic Domain
  • Coumarins / chemical synthesis*
  • Coumarins / chemistry
  • Coumarins / pharmacology
  • Cyclic Nucleotide Phosphodiesterases, Type 3
  • Humans
  • In Vitro Techniques
  • Models, Molecular
  • Morpholines / chemical synthesis*
  • Morpholines / chemistry
  • Morpholines / pharmacology
  • Phosphodiesterase Inhibitors / chemical synthesis*
  • Phosphodiesterase Inhibitors / chemistry
  • Phosphodiesterase Inhibitors / pharmacology
  • Piperazines / chemical synthesis*
  • Piperazines / chemistry
  • Piperazines / pharmacology
  • Platelet Aggregation Inhibitors / chemical synthesis*
  • Platelet Aggregation Inhibitors / chemistry
  • Platelet Aggregation Inhibitors / pharmacology

Substances

  • 8-methyl-4-(1-piperazinyl)-7-(3-pyridylmethoxy)coumarin
  • 8-methyl-7-(2-morpholinoethoxy)-4-(1-piperazinyl)-2H-1-benzopyran-2-one
  • Coumarins
  • Morpholines
  • Phosphodiesterase Inhibitors
  • Piperazines
  • Platelet Aggregation Inhibitors
  • 3',5'-Cyclic-AMP Phosphodiesterases
  • Cyclic Nucleotide Phosphodiesterases, Type 3
  • PDE3A protein, human