Electrochemical oxidation of N-substituted 1,4- and 1,2-dihydropyridine derivatives

AbstractThe electrochemical oxidation and reduction properties of different dihydropyridines and pyridines have been investigated in non aqueous solvent as benzonitrile and aceto-nitrile with tetra-n-butylammonium perchlorate as supporting electrolyte at platinium electrodes using DC-voltametry, cycl. voltametry and coulometry. Possible redox-mechanisms are discussed.

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Electrochemical and biological oxidation of 1,4-dihydropyridine derivatives

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19811141 ◽

1981 ◽

Vol 46 (5) ◽

pp. 1141-1147 ◽

Cited By ~ 3

Author(s):

Antonín Kurfürst ◽

Jiří Ludvík ◽

Pavel Rauch ◽

Miroslav Marek

Keyword(s):

Electrochemical Reduction ◽

Nitro Group ◽

Electrochemical Oxidation ◽

Respiratory Chain ◽

Enzyme System ◽

Biological Oxidation ◽

Common Trends ◽

Cyclic Voltametry ◽

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.

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Substituent effect in electrochemical and ferricyanide oxidations of para-substituted 1-benzyl-3-carbamoyl-1,4-dihydropyridines

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19831408 ◽

1983 ◽

Vol 48 (5) ◽

pp. 1408-1421 ◽

Cited By ~ 4

Author(s):

Františka Pavlíková-Raclová ◽

Josef Kuthan

Keyword(s):

Electrochemical Oxidation ◽

Rate Constants ◽

Substituent Effect ◽

Potassium Ferricyanide ◽

Rotating Disc Electrode ◽

Disc Electrode ◽

Rotating Disc ◽

Half Wave ◽

Substituted 1 ◽

Dihydropyridine Derivatives

Half-wave potentials E1/2 of electrochemical oxidation of the title 1,4-dihydropyridine derivatives with the substituents N(CH3)2, OCH3, CH3, H, F, Cl, COOCH3, and CN have been measured on platinum rotating disc electrode in aqueous and anhydrous dimethylformamide, and apparent rate constants k2 of their oxidation with potassium ferricyanide have been measured in water at 298 K. The two quantities (E1/2 and k2) have been correlated both mutually and with empirical σp constants of the substituents. The found correlation relations have been discussed with respect to mechanism of the two transformations investigated.

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