Design And Synthesis Of 3-Benzoyl-2H-1-Benzopyran-2-one And Its α-Glucosidase Inhibitory Activity

The action mechanisms ofα-glucosidase inhibitors and theri reseach progress inα-glucosidase inhibitors were reviewed briefly in this thesis. It is proved that diabetes mellitus usually appears after postprandial hyperglycaemia.α-Glucosidase inhibitors could effectively control of postprandial hyperglycaemia via inhibiting oligosaccharides decompositioning into monosaccharides.The aim of our study is to find novelα-glucosidase inhibitors with high activity. Based on the structure features of sulfonamide chalcones and flavones withα-glucosidase inhibitory activities and their mechanisms onα-glucosidase,3-benzoyl-2H-1-benzopyran-2-one derivatives were designed.4-Nitrobenzoic acid was acylated with thionyl chloride to give 4-nitrobenzoyl chloride, and then reacted with acylation ethyl acetoacetate, followed by hydrolysis, giving ethyl 3-(4-nitro)phenyl-3-oxopropanoate, which was reducted to give ethyl 3-(4-amino)phenyl-3-oxopropanoate, the product and then was acylated with benzene sulfonyl chloride and benzoyl chloride respectively, giving ethyl 3-[(4-phenylsulfonyl)amido] 3-oxophenylpropanoate and ethyl 3-[(4-benzoyl)amido] 3-oxophenylpropanoate, then reacted with substituted salicylic aldehyde via Knoevernagel condensation, 20 target compounds were obtained. The structures of the compounds synthesized were confirmed by ~1H-NMR and IR.The inhibitory activities of target compounds were evaluated with yeastα-glucosidase. It was proved that most of the 3-[4-(phenylsulfonyl)amido]benzoyl-2H-1-benzopyran-2-one derivatives showed good inhibitory activity, the IC50 values range from 0.199μM to 7.180μM, however most of the 3-[4- (benzoyl)amido]benzoyl-2H-1-benzopyran-2-one derivatives seemed no activities.