Pyranochromenone derivatives 3a–d, 6a–j and 2H-chromenones 8a–b were synthesized and screened for their in vitro α-amylase inhibitory and ABTS•+ [2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)] free radical scavenging activities. Compounds 3a, 3c, and 6d displayed dual function of ABTS•+ radical scavenging as well as α-amylase inhibition. Compound 6h was found to be most potent α-amylase inhibitor in present series of compounds. Docking studies suggest that these compounds occupy active site of the human pancreatic α-amylase similar to that of acarbose which inhibits enzyme by hydrophobic interactions. These compounds have potential to be developed as therapeutics targeted against diet-induced hyperglycemia in diabetes. Series of pyranochromenone derivatives 3a–d, 6a–j, and 8a–b were synthesized, among these compound 6h shown potent intestinal α-amylase inhibitory activity. Compounds 3a, 3c, and 6d were shown dual properties such as α-amylase inhibitory and antioxidant activities. These derivatives may serve as a model compounds for design and development of therapeutics based agents.