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Amino substituted benzamide derivatives as potential antioxidants

In the last few decades, the search for the novel antioxidants led to the synthesis or isolation of different organic molecules which showed promising and more effective antioxidant activity in comparison with the standard antioxidants, such as vitamins C and A or BHT[1]. We prepared a range of N-arylbenzamides with a variable number of methoxy and hydroxy groups, bearing either amino or amino protonated moieties, and used DPPH and FRAP assays to evaluate their antioxidant capacity[2]. Most of the systems exhibit improved antioxidative properties relative to the reference BHT molecule in both assays. Combining results from both sets of experiments, the most promising antioxidative potential was displayed by the trihydroxy derivative, which we propose as a lead compound for a further optimization of the benzamide scaffold. Computational analysis helped in interpreting the observed trends and demonstrated that protonated systems are better antioxidants than their neutral counterparts, while underlying the positive influence of the electron-donating methoxy group on the antioxidant properties, thus confirming the experiments. It also revealed that the introduction of the hydroxy groups shifts the reactivity from both amide and amine groups towards this moiety and additionally enhances antioxidative features.

benzamide derivatives ; antioxidative potential ; computational study

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