Synthesis and biological evaluation of 3-styrylchromone derivatives as free radical scavengers and α-glucosidase inhibitors.

A series of 3-styrylchromone derivatives (4-20) were synthesized and the structure-activity relationships for α-glucosidase inhibition and antioxidant activities were analyzed. Among the synthesized compounds, compounds 15 and 20, which contain a catechol moiety, showed both potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity (15: EC₅₀=17 µM; 20: EC₅₀=23 µM) and α-glucosidase inhibitory activity (15: IC₅₀=16 µM; 20: IC₅₀=10 µM). Our data suggest that 3-styrylchromone derivatives are novel α-glucosidase inhibitors that have the potential to counteract diet-induced hyperglycemia in diabetes.