Synthesis, DPPH and ABTS Activity of Novel Furfuryl-Chalcone Derivatives

Abstract

In this study, novel furfuryl-chalcone derivatives substituted sulfonyl chloride or sulphonamide were synthesized. Their antioxidant properties were investigated via DPPH and ABTS assays. All furfuryl-chalcones had high antioxidant properties. Among them, (E)-5-(3-(4-(chlorosulfonyl)-3-hydroxyphenyl)-3-oxoprop-1-en-1-yl)furan-2-sulfonyl chloride (4e) and (E)-5-(3-(3-(chlorosulfonyl)-4-hydroxyphenyl)-3-oxoprop-1-en-1-yl)furan-2-sulfonyl chloride (4d) exhibited the highest DPPH activity with the IC50 values of 4.23 ?M and 6.68 ?M, respectively, which are almost 2- and 1.5-fold more than quercetin activity (IC50 = 8.69 ?M), well-known as antioxidant agent and used as a standard. Also, 4e and 4d had the highest ABTS activity with the IC50 value of 5.55 ?M and 7.84 ?M, respectively, which are almost 2.8- and 2-fold higher than that of quercetin (IC50 = 15.49 ?M). The structure-activity relationship results revealed that most of synthesized sulfonyl chloride derivatives (4a-e) have higher antioxidant activity than the sulphonamide derivatives (5a-c) and also 4d and 4e, including hydroxyl group, exhibited the strongest antioxidant activity as expected.