Organic nitrates. II. Synthesis and biological activities of 4-nitrooxymethylphenyl-1,4-dihydropyridines.
Both 2-nitrooxymethyl-4-phenyl- (2) and 4-nitrooxymethylphenyl-1,4-dihydropyridines (3) represent new combinations of two different vasodilating structures. 2 could not be isolated due to its spontaneous lactonization. Derivatives of 3 were obtained via Hantzsch synthesis using nitrooxymethylated benzaldehydes. The inotropic potency in isolated porcine trabecular muscles and the vasodilator activity in isolated porcine coronary arteries of four nitrooxyphenyl-dihydropyridines were determined. Nitrendipine (NTD) and glyceryl trinitrate (GTN) were used for reference. 3 were negative inotropic, however, less than NTD and--except for the dicyano derivative 3d--more than GTN. Vasodilator properties were less pronounced than that of both nitrendipine and GTN. Vascular selectivity was low.
Lehmann
J
J
Pharmazeutisches Institut, Universität Bonn, Germany.
Kahlich
R
R
Meyer zum Gottesberge
C
C
Fricke
U
U
D000818:Animals; D002121:Calcium Channel Blockers / Q000138:chemical synthesis* / Q000494:pharmacology*; D002316:Cardiotonic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000494:pharmacology*; D066298:In Vitro Techniques; D013552:Swine; D014665:Vasodilator Agents / Q000138:chemical synthesis / Q000494:pharmacology
D002121:Calcium Channel Blockers; D002316:Cardiotonic Agents; D004095:Dihydropyridines; D014665:Vasodilator Agents