Oxidation of C4-hydroxyphenyl 1,4-dihydropyridines in dimethylsulfoxide and its reactivity towards alkylperoxyl radicals in aqueous medium.
This work reports the electrochemical oxidation of three newly synthesized C4-hydroxyphenyl-substituted 1,4-dihydropyridine derivatives in dimethylsulfoxide. The reactivity of the compounds with ABAP-derived alkylperoxyl radicals in aqueous buffer pH 7.4, was also studied. The oxidation mechanism involves the formation of the unstable dihydropyridyl radical, which was confirmed by controlled-potential electrolysis (CPE) and ESR experiments. The final product of the CPE, that is, pyridine derivative, was identified by GC-MS technique for the three derivatives. A direct reactivity of the synthesized compounds toward ABAP-derived alkylperoxyl radicals was found. The pyridine derivative was identified by GC-MS as the final product of the reaction. Results reveal that this type of 1,4-DHPs significantly reacts with the radicals, even compared with commercial 1,4-DHP drugs with a well-known antioxidant ability.
Núñez-Vergara
Luis J
LJ
Laboratory of Biolectrochemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Santiago, Chile. lnunezv@ciq.uchile.cl
Salazar
R
R
Camargo
C
C
Carbajo
J
J
Conde
B
B
Navarrete-Encina
P A
PA
Squella
J A
JA
D004095:Dihydropyridines / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D004578:Electron Spin Resonance Spectroscopy; D005609:Free Radicals; D008401:Gas Chromatography-Mass Spectrometry; D010084:Oxidation-Reduction; D013056:Spectrophotometry, Ultraviolet; D014867:Water
D004095:Dihydropyridines; D005609:Free Radicals; D014867:Water; C038806:1,4-dihydropyridine; D004121:Dimethyl Sulfoxide