Synthesis, crystal structure, and in vitro evaluation of newer 2,4-thiazolidinedione hybrids as α-glucosidase inhibitors

新型2,4-噻唑烷二酮杂合物作为α-葡萄糖苷酶抑制剂的合成、晶体结构及体外评价

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Abstract

BACKGROUND: In our continued efforts to explore newer inhibitors for AG to treat T2DM, we report the design and synthesis of a new library of VD-TZD hybrids employing a flexible and efficient synthetic approach for structural modification. MATERIALS & METHODS: Physicochemical, SC-XRD, and spectral analyses were performed to characterize the synthesized compounds and evaluate their in vitro AG inhibitory activity. RESULTS: Compared to Acarbose, VD-TZD hybrids displayed good AGI activity. Compounds 6f and 6g exhibited the strongest inhibitory activities against AG with IC(50) values of 18.16 ± 0.41 and 19.59 ± 0.78 μM. Compounds 6f and 6g exhibited an improved binding affinity for AG (PDB ID: 5NN8), with docking scores of -7.50 and -7.46 kcal/mol, respectively. The carbonyl group of compounds 6f and 6g formed hydrogen bonds with the amino acid residues LEU677, LEU678, and ARG411. The cell cytotoxicity assay indicated that compound 6f exhibited low cytotoxic activity against HEK-293 cell lines. The in silico ADMET profile of compound 6f indicates satisfactory oral drug-likeness and the absence of toxic effects. CONCLUSION: In conclusion, compound 6f could be considered a promising lead compound for further optimization in AGI development for the treatment of T2DM.

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