Synthesis and Biological Evaluation of 3-Benzylidene-4-chromanone Derivatives as Free Radical Scavengers and α-Glucosidase Inhibitors

抄録

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.