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Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals

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2008-10-01
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Salazar González, Ricardo Andrés
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Electrochemical oxidation of C4-vanillin- and C4-isovanillin-1,4-dihydropyridines in aprotic medium: Reactivity towards free radicals
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Author
  • Salazar González, Ricardo Andrés;
  • Navarrete Encina, Patricio;
  • Camargo Grandón, Rodrigo;
  • Squella Serrano, Juan;
  • Núñez Vergara, Luis;
Abstract
This work reports the electrochemical oxidation of two new synthetic C4-vanillin and -isovanillin-1,4-dihydropyridines in aprotic medium. Its reactivity with alkylperoxyl radicals ABAP-derived at pH 7.4 is also studied. Voltammetry, coulometry, controlled-potential electrolysis, UV-visible spectroscopy and GC-MS techniques were employed to collect data that permitted us to study its oxidation. Effect of TBA-OH addition on the oxidation was electrochemically and spectroscopically followed. In aprotic medium, the oxidation mechanism involves the formation of the pyridine derivative, which was generated by controlled-potential electrolysis (CPE) at 1270 mV and identified by GC-MS technique as the final product of the electrolysis. Spectroelectrochemical experiments also support the formation of the pyridine derivative from the oxidation of both 1,4-dihydropyridines. Direct reactivity of synthesized compounds towards alkylperoxyl radicals ABAP-derived was determined. Results reveal that the inclusion of vanillin radical or its positional isomer, isovanillin in the 4-position of the dihydropyridine ring produced a significant positive effect on the reactivity towards alkylperoxyl radicals, even compared with commercial dihydropyridine drugs with a well-known antioxidant ability. Scavenging mechanism involves the electron-transfer and the formation of a pyridine derivative, which was identified by GC-MS.
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URI: https://repositorio.uchile.cl/handle/2250/120757
ISSN: 1572-6657
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JOURNAL OF ELECTROANALYTICAL CHEMISTRY 622(1): 29-36
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