Abstract A sequence of substituted phosphonates containing the thiazolidinedione moiety was synthesized with good yields. The structures of all the synthesized compounds were confirmed by NMR (31P, 1H and 13C) and IR spectroscopy, mass spectrometry and C, H, N elemental analyses. In silico molecular docking study was also carried out to evaluate their interaction and binding modes on ligands against human PPAR γ protein for their anti-diabetic activity. From the docking results, it was determined that the compounds (Z)-dimethyl 5-(3-nitrobenzylidene)−2,4-dioxothiazolidin-3-ylphosphonate (7a), (Z)-dimethyl 5-(3-chloro-4-fluorobenzylidene)−2,4-dioxothiazolidin-3-ylphosphonate (7f), (Z)-dimethyl 5-(2,4-dichlorobenzylidene)−2,4-dioxothiazolidin-3-ylphosphonate (7e) and (Z)-dimethyl 5-((5-methoxypyridin-2-yl)methylene)−2,4-dioxothiazolidin-3-ylphosphonate (7j) have shown better binding energies (−7.8, −7.6, −7.5 and −7.6 Kcal/mol) with the target gene, PPAR γ than the reference drug, Rosiglitazone (−7.4 Kcal/mol). In vitro anti-diabetic activity of the title compounds was also screened by standard α-amylase inhibition assay. Some of the tested compounds proved to possess promising activity when compared with the reference drug. Graphical Abstract

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含噻唑烷二酮部分的膦酸酯的合成及抗糖尿病活性评价

摘要 以良好的收率合成了一系列含有噻唑烷二酮部分的取代膦酸酯。所有合成化合物的结构均通过 NMR（31P、1H 和 13C）和红外光谱、质谱和 C、H、N 元素分析证实。还进行了计算机分子对接研究，以评估它们在抗人 PPAR γ 蛋白配体上的相互作用和结合模式的抗糖尿病活性。从对接结果确定化合物(Z)-二甲基5-(3-硝基苯亚甲基)-2,4-二氧噻唑烷-3-基膦酸酯(7a)、(Z)-二甲基5-(3-氯-4 -氟苯亚甲基)-2,4-二氧噻唑烷-3-基膦酸酯 (7f), (Z)-二甲基 5-(2,4-二氯苯亚甲基)-2,4-二氧噻唑烷-3-基膦酸酯 (7e) 和 (Z)-二甲基5-((5-甲氧基吡啶-2-基)亚甲基)-2，4-dioxothiazolidin-3-ylphosphonate (7j) 与目标基因 PPAR γ 的结合能（-7.8、-7.6、-7.5 和 -7.6 Kcal/mol）比参考药物罗格列酮（-7.4 Kcal/mol）更好）。标题化合物的体外抗糖尿病活性也通过标准 α-淀粉酶抑制试验进行筛选。与参考药物相比，一些测试化合物证明具有良好的活性。图形概要