Electrochemical and biological oxidation of 1,4-dihydropyridine derivatives
Electrochemical oxidation of 1,4-dihydropyridines I-XII and electrochemical reduction of the nitro group of 4-(2-nitrophenyl)-1,4-dihydropyridines III, VI, IX and XII was studied using cyclic voltametry. When comparing the electrochemical and the biological oxidation of 3,5-dimethoxycarbonyl-2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine (IX, Nifedipine) and related 1,4-dihydropyridines it was found that in spite of certain common trends the oxidation of these compounds (I-XII) in the organism cannot be predicted unambiguously. Of the substances tested compounds IX and XI (3,5-diethoxycarbonyl-4-phenyl-2,6-dimethyl-1,4-dihydropyridine) were the least oxidizable by the respiratory chain, and at the same time they did not inhibit this enzyme system. In addition to this, compound IX was the least oxidizable by the microsomal system.