<br>4-噻唑烷酮衍生物的合成、表征、抗糖化评价、分子对接和 ADMET 研究,ACS Omega

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4-噻唑烷酮衍生物的合成、表征、抗糖化评价、分子对接和 ADMET 研究
ACS Omega ( IF 3.7 ) Pub Date : 2023-12-28 , DOI: 10.1021/acsomega.3c08463
Ashanul Haque _{1,

2} , Mohd Wajid Ali Khan _{1,

2} , Khalaf M Alenezi _{1,

2} , Raoudha Soury _{1,

2} , Muhammad S Khan ₃ , Shahzaib Ahamad ₄ , Md Mushtaque ₅ , Dinesh Gupta ₄

Affiliation

新型小分子糖化抑制剂的设计和开发对于预防各种慢性疾病至关重要，包括糖尿病、免疫炎症、心血管和神经退行性疾病。 4-Thiazolidinone 或 thiazolidine-4-one 是一种众所周知的杂环化合物，具有抑制晚期糖基化终产物形成的潜力。在目前的工作中，我们报告了四种新的5-亚芳基3-环丙基-2-(苯基亚氨基)噻唑烷-4-酮( 1-4 )化合物的合成和表征及其人血清白蛋白糖化抑制活性。其中一种化合物 5-(2 H -1,3-苯并间二氧杂环己烷-5-基亚甲基)-3-环丙基-2-(苯基亚氨基)-1,3-噻唑烷-4-酮 ( 3 ) 在合成中显示出有效的抑制作用糖化反应的初始产物、中间产物和最终产物。此外，还发现α-螺旋和β-片层的构象变化（由于高血糖）在添加( 3 )后发生逆转。实验结果得到了计算[分子对接、ADME/Tox 和密度泛函理论 (DFT)] 研究的补充。化合物的对接分数的顺序为1 > 3 > 2 > 4 ，表明5-亚芳基部分极性基团的重要性。 ADME/Tox和DFT计算结果揭示了化合物的安全性，具有较高的药物相似性和稳定性。总的来说，我们推测这项研究的结果可以为 4-噻唑烷酮类的生物活性提供有价值的见解。

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Synthesis, Characterization, Antiglycation Evaluation, Molecular Docking, and ADMET Studies of 4-Thiazolidinone Derivatives

The design and development of new small-molecule glycation inhibitors are essential for preventing various chronic diseases, including diabetes mellitus, immunoinflammation, cardiovascular, and neurodegenerative diseases. 4-Thiazolidinone or thiazolidine-4-one is a well-known heterocyclic compound with the potential to inhibit the formation of advanced glycation end products. In the present work, we report the synthesis and characterization of four new 5-arylidene 3-cyclopropyl-2-(phenylimino)thiazolidin-4-one (1–4) compounds and their human serum albumin glycation inhibitory activity. One of the compounds 5-(2H-1,3-benzodioxol-5-ylmethylidene)-3-cyclopropyl-2-(phenylimino)-1,3-thiazolidin-4-one (3) showed potent inhibition in the synthesis of initial, intermediary, and final products of glycation reactions. Besides, conformational changes in the α-helix and β-sheet (due to hyperglycemia) were also found to be reversed upon the addition of (3). Experimental findings were complemented by computational [molecular docking, ADME/Tox, and density functional theory (DFT)] studies. The docking scores of the compounds were in order 1 > 3 > 2 > 4, indicating the importance of the polar group at the 5-arylidene moiety. The results of ADME/Tox and DFT calculations revealed the safe nature of the compounds with high drug-likeness and stability. Overall, we speculate that the results of this study could provide valuable insights into the biological activity of 4-thiazolidinones.

更新日期：2023-12-28

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