Collect. Czech. Chem. Commun. 1981, 46, 1141-1147

Electrochemical and biological oxidation of 1,4-dihydropyridine derivatives

Antonín Kurfürsta, Jiří Ludvíkb, Pavel Rauchc and Miroslav Marekc

a Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6
b The J. Heyrovský Institute of Physical Chemistry and Electrochemistry, Czechoslovak Academy of Sciences, 121 38 Prague 2
c Department of Biochemistry and Microbiology, Prague Institute of Chemical Technology, 166 28 Prague 6


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.