ESR and electrochemical study of 5-nitroindazole derivatives with antiprotozoal activity.
The electrochemistry of 3-alkoxy- and 3-hydroxy-1-[omega-(dialkylamino)alkyl]-5-nitroindazole derivatives were characterized using cyclic voltammetry in DMSO. The nitro reduction process was studied and this was affected by the acid moieties present in these compounds. A nitro anion self-protonation process was observed. This phenomenon was studied by cyclic voltammetry in presence of increasing amount of NaOH. The reactivity of the nitro anion radical of these derivatives with glutathione was also studied by cyclic voltammetry. The oxidizing effect of glutathione is supported by the parallel decrease of the anodic peak current and increase of the cathodic peak in the cyclic voltammograms, corresponding to the wave of the nitro anion radical from uncharged species with the addition of glutathione. Nitro anion radicals obtained by electrolytic reduction of these derivatives were measured and analyzed in DMSO using electron spin resonance spectroscopy.
Olea-Azar
Claudio
C
Departamento de Química Inorgánica y Analítica, Facultad de Ciencias Químicas y Farmacéuticas, Universidad de Chile, Chile. colea@uchile.cl
Cerecetto
Hugo
H
Gerpe
Alejandra
A
González
Mercedes
M
Arán
Vicente J
VJ
Rigol
Carolina
C
Opazo
Lucía
L
D000838:Anions / Q000737:chemistry; D000981:Antiprotozoal Agents / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D004563:Electrochemistry; D004578:Electron Spin Resonance Spectroscopy; D005978:Glutathione / Q000737:chemistry; D007191:Indazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D009574:Nitro Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
D000838:Anions; D000981:Antiprotozoal Agents; D007191:Indazoles; D009574:Nitro Compounds; D005978:Glutathione; D004121:Dimethyl Sulfoxide