Diabetes mellitus is a ubiquitous challenge and accounts for 387 million patients globally and this figure will ascent to over 590 million by the year 2035. α-Glucosidase inhibitors results in decrease in postprandial blood glucose level by delaying of glucose absorption. Two series of substituted benzopyran-2-one derivatives were appraised by molecular docking studies, drug-likeness and ADMET properties predictions. Compounds 8, 10, 19, 21 exhibited strong binding interactions such as hydrogen bonding, hydrophobic and electrostatic interactions with 3D α-glucosidase modeled protein because of presence of OH group at R2 position. Top most active compound 21 (7-hydroxy-6-methoxy-3-[4-(4-methyl-phenylsulfonamido)benzoyl]-2H-1-benzopyran-2- one) interacted with protein by forming 3 hydrogen bonding and pi-pi stacked, pi-pi T shaped, pi-alkyl and pi-anion interactions. The consequences of in silico pharmacokinetic inferred their potential as potent α-glucosidase inhibitor.