Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines

J Med Chem. 1990 May;33(5):1510-5. doi: 10.1021/jm00167a035.

Abstract

2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Calcium Channel Blockers / chemical synthesis*
  • Chemical Phenomena
  • Chemistry
  • Dihydropyridines / pharmacology
  • Guinea Pigs
  • Molecular Conformation
  • Muscle, Smooth, Vascular / drug effects
  • Muscle, Smooth, Vascular / metabolism
  • Nitrendipine / antagonists & inhibitors
  • Nitrendipine / metabolism
  • Pyrimidines / chemical synthesis*
  • Pyrimidines / pharmacology
  • Rabbits
  • Rats
  • Rats, Inbred SHR
  • Structure-Activity Relationship

Substances

  • Calcium Channel Blockers
  • Dihydropyridines
  • Pyrimidines
  • Nitrendipine