Discovery of potent cyclic GMP phosphodiesterase inhibitors. 2-Pyridyl- and 2-imidazolylquinazolines possessing cyclic GMP phosphodiesterase and thromboxane synthesis inhibitory activities

J Med Chem. 1995 Sep 1;38(18):3547-57. doi: 10.1021/jm00018a014.

Abstract

Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2-phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP-PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3-pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.

MeSH terms

  • 3',5'-Cyclic-GMP Phosphodiesterases / antagonists & inhibitors*
  • 3',5'-Cyclic-GMP Phosphodiesterases / metabolism
  • Adult
  • Animals
  • Blood Platelets / cytology
  • Blood Platelets / enzymology
  • Cattle
  • Cells, Cultured
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology
  • Humans
  • Male
  • Quinazolines / chemistry
  • Quinazolines / pharmacology*
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Thromboxane A2 / biosynthesis*
  • Thromboxane-A Synthase / antagonists & inhibitors

Substances

  • Cyclooxygenase Inhibitors
  • Quinazolines
  • Thromboxane A2
  • 3',5'-Cyclic-GMP Phosphodiesterases
  • Thromboxane-A Synthase