Synthesis, α-glucosidase inhibitory and molecular docking studies of prenylated and geranylated flavones, isoflavones and chalcones

Abstract Three series of prenylated and/or geranylated flavonoids were synthesized and evaluated for their α-glucosidase inhibitory activity. The 3′,5′-digeranylated chalcone ( 16 ) was identified as a new α-glucosidase inhibitor whose activity (IC 50  = 0.90 μM) was 50-fold more than that of acarbose (IC 50  = 51.32 μM). Molecular docking studies revealed the existence of strong hydrophobic interaction and H-bonding between compound 16 and α-glucosidase’s active site. The inhibitory mode analysis showed that 16 exhibited a competitive inhibitory mode.