New 1,4-dihydropyridines endowed with NO-donor and calcium channel agonist properties

J Med Chem. 2004 May 6;47(10):2688-93. doi: 10.1021/jm031109v.

Abstract

A new series of calcium channel agonists structurally related to Bay K8644, containing NO donor furoxans and the related furazans unable to release NO, is described. The racemic mixtures were studied for their action on L-type Ca(2+) channels expressed in cultured rat insulinoma RINm5F cells. All the products proved to be potent calcium channel agonists. All the racemic mixtures, with the only exception of the carbamoyl derivatives 9, 12 endowed with scanty solubility, were separated by chiral chromatography into the corresponding enantiomers; the (+) enantiomers were found to be potent agonists while the (-) ones were feeble antagonists. The racemic mixtures were also assessed for their positive inotropic activity on electrically stimulated rat papillary muscle and for their ability to increase Ca(2+) entry into the vascular smooth muscle of rat aorta strips. The cyanofuroxan 8 proved to be an interesting product with dual Ca(2+)-dependent positive inotropic and NO-dependent vasodilating activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aorta, Thoracic / drug effects
  • Aorta, Thoracic / physiology
  • Calcium Channels, L-Type / drug effects*
  • Calcium Channels, L-Type / physiology
  • Cell Line, Tumor
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry
  • Dihydropyridines / pharmacology
  • In Vitro Techniques
  • Male
  • Muscle, Smooth / drug effects
  • Muscle, Smooth / physiology
  • Nitric Oxide Donors / chemical synthesis*
  • Nitric Oxide Donors / chemistry
  • Nitric Oxide Donors / pharmacology
  • Papillary Muscles / drug effects
  • Papillary Muscles / physiology
  • Patch-Clamp Techniques
  • Rats
  • Rats, Wistar
  • Stereoisomerism
  • Vasodilator Agents / chemical synthesis*
  • Vasodilator Agents / chemistry
  • Vasodilator Agents / pharmacology

Substances

  • Calcium Channels, L-Type
  • Dihydropyridines
  • Nitric Oxide Donors
  • Vasodilator Agents