Synthesis and biological evaluation of 3-benzylidene-4-chromanone derivatives as free radical scavengers and α-glucosidase inhibitors

Abstract

A series of 3-benzylidene-4-chromanone derivatives (3-20) were synthesized and the structure-activity relationships for antioxidant and α-glucosidase inhibitory activities were evaluated. Among synthesized compounds, compounds 5, 13, 18, which contain catechol moiety, showed the potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (5: EC50 13 μM; 13: EC50 14 μM; 18: EC50 13 μM). The compounds 12, 14, 18 showed higher α-glucosidase inhibitory activity (12: IC50 15 μM; 14: IC50 25 μM; 18: IC50 28 μM). The compound 18 showed both of potent DPPH radical scavenging and α-glucosidase inhibitory activities. These data suggest that 3-benzylidene-4-chromanone derivatives, such as compound 18, may serve as the lead compound for the development of novel α-glucosidase inhibitors with antioxidant activity.