A new series of biscoumarin derivatives 3a–n were synthesized and evaluated for their α-glucosidase inhibitory activities. The reaction of the 4-aminocoumarin with benzaldehyde derivatives led to the formation of the title compounds in good yields. All the synthesized compounds showed potent α-glucosidase inhibitory activity with IC₅₀ ranging from 20.0 ± 0.7 to180.1 ± 0.8 µM, in comparison with acarbose as the standard drug (IC₅₀ = 750.0 1.5 µM). Among the synthesized compounds, 3,3'-(p-tolylmethylene)bis(4-amino-2H-chromen-2-one) 3c was found to be the most active compound with an IC₅₀ value of 20.0 ± 0.7 µM. Kinetic study exhibited that compound 3c was a competitive inhibitor against α-glucosidase (K_i = 22.4 µM). In silico docking study for the most potent compound 3c was also performed.