Reactivity of C4‐indolyl substituted 1,4‐dihydropyridines toward superoxide anion (O2•) in dimethylsulfoxide |
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| Authors: | Ricardo Salazar P. A. Navarrete‐Encina J. A. Squella C. Camargo Luis J. Nú?ez‐Vergara |
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| Affiliation: | 1. Laboratory of Bioelectrochemistry, University of Chile, Santiago, Chile;2. Laboratory of Organic Synthesis and Molecular Modeling, University of Chile, Santiago, Chile;3. Laboratory of Antidoping, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Santiago, Chile |
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| Abstract: | Reactivity of two new C4‐indolyl substituted 1,4‐dihydropyridines (1,4‐DHPs) toward superoxide anion (O2? ) in dimethylsulfoxide (DMSO) is reported. Reactivity was followed by electrochemical and spectroscopic techniques. Gas chromatography‐mass spectrometry (GC–MS) was used to identify the final products of the reaction. C4 indolyl‐substituted‐1,4‐DHPs reacted toward O2? at significant rates, according to the calculated kinetic rate constants. Results are compared with 4‐phenyl‐DHP and the commercial 1,4‐DHPs, nimodipine, nisoldipine, and amlodipine. Indolyl‐substituted 1,4‐DHPs were more reactive than the commercial derivatives. The direct participation of proton of the 1‐position of the secondary amine in the quenching of O2? was demonstrated. Copyright © 2008 John Wiley & Sons, Ltd. |
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| Keywords: | C4‐indolyl substituted 1,4‐dihydropyridines superoxide radical anion reactivity cyclic voltammetry UV– Visible spectroscopy first‐order kinetic rate constants |
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