Synthesis and electrochemical and antioxidant properties of chalcogenocyanate oxadiazole and 5-heteroarylchalcogenomethyl-1H-tetrazole derivatives

Abstract

This article presents the chalcogenocyanate oxadiazoles 7 and 8 and their derivatives 5-heteroarylchalcogenomethyl-1H-tetrazoles 9 and 10, which were synthesized in high yields. The 5-substituted-1H-tetrazoles were obtained via [3+2] cycloaddition reactions of chalcogenocyanates 7 and 8 with sodium azide (NaN₃) using a simple methodology. All the obtained compounds were characterized by NMR and high resolution mass spectrometry analysis. Their in vitro antioxidant activity was evaluated by measuring their ability to eliminate free radicals in the form of 2,2-diphenyl-2-picrylhydrazyl (DPPH) and through the reduction of molybdenum(VI) to molybdenum(V). The results for the phosphomolybdenum method indicated that some compounds have antioxidant properties, as evidenced by electrochemical oxidation tests to which they were subjected, which correlate their oxidation potentials (E_pa) with their activity values (EC₅₀).