Synthesis and biologic activity of bis and mono nitrophenyl substituted ferrocene and their interaction with O2/O2- redox couple using cyclic voltammetry

S. Benabdesselam, O. Rahim

Abstract


Abstract: In this work, 3-nitrophenylferrocene (3-NPF) and bis-3-nitrophenylferrocene (bis-3-NPF) were synthesized through the arylation of ferrocene by diazotasing of 3-nitroaniline by sodium nitrite in the presence of H2SO4 to form meta-nitrobenzendiazonium sulfide. The synthesized compounds were characterized by IR infrared and NMR magnetic resonance spectroscopy (1H, 13C and DEPT). The superoxide scavenging effect was assessed by electrochemical assay; cyclic voltammetry, the DPPH scavenging assay and total antioxidant capacity were assessed using spectrophotometric assay. In this paper, the antioxidant capacity index (IC50) towards supreroxide anion radical, DPPH radical and TAC were determined, we found that the IC50 of compounds against superoxide ranged from 1.212 to 2.709mg/ml, the lowest value of IC50 was detected in bis-3-NPF, the DPPH radical inhibition capacities are in the order of ascorbic acid˃α-Tocopherol˃bis-3-NPF˃3-NPF˃ with IC50 respectively of 0.0063mg/ml, 0.0134mg/ml, 0.773mg/ml and 1. 44mg/ml and the maximum Mo(VI)  reducing activity was observed at high concentrations (0.8 mg/ml), the TAC of the compounds was found to be in the following order: Bis-3-NPF ˃ 3-NPF. The antioxidant activity coefficients (Ka), the interaction coefficients (Kb) and the binding free energy of these two ferrocene derivatives towards the superoxide radical were determined using the values of the intensities of the anodic currents from the cyclic voltammograms of the O2/O2- couple.

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