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

Three series of prenylated and/or geranylated flavonoids were synthesized and evaluated for their alpha-glucosidase inhibitory activity. The 3',5'-digeranylated chalcone (16) was identified as a new alpha-glucosidase inhibitor whose activity (IC50 = 0.90 mu M) was 50-fold more than that of acarbose (IC50 = 51.32 mu M). Molecular docking studies revealed the existence of strong hydrophobic interaction and H-bonding between compound 16 and alpha-glucosidase's active site. The inhibitory mode analysis showed that 16 exhibited a competitive inhibitory mode. (C) 2015 Elsevier Ltd. All rights reserved.