Compounds containing a trimethoxy benzyl or thiosemicarbazide moiety have previously been shown to demonstrate strong activity in several types of antioxidant assays. In the current study, fourteen trimethoxy benzyl-aryl thiosemicarbazide hybrid compounds were synthesized and evaluated for their antioxidant effects using the Cupric, Cu(II), Reducing Antioxidant Capacity (CUPRAC) method. The hybrid compounds were prepared in four steps, with each compound containing a phenyl or a substituted phenyl group as part of the thiosemicarbazide moiety. The effect of the nature of the substituent, electron-donating vs electron-withdrawing, on the extent of copper (II) ion reduction was determined using UV-Vis spectroscopy. The molar absorptivity of each compound was compared against that of Trolox to determine the Trolox Equivalent Antioxidant Capacity (TEAC) coefficient. Of the fourteen trimethoxy benzyl-thiosemicarbazide hybrid compounds evaluated, eleven displayed better copper (II) reducing ability than Trolox, with the most active compound displaying a TEAC coefficient of 2.4.

Synthesis and antioxidant evaluation of trimethoxy benzyl-thiosemicarbazide hybrids

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