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Synthesis and structural confirmation on selective N-alkylation of (Z)-5-((5-chloro- 1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues with their molecular docking studies
Indian Journal of Chemistry, Section B ( IF 0.456 ) Pub Date : 2021-09-29
Vasappanavara Sreenatha, Karnam Jayarampillai Rajendra Prasad

In the present investigation, a series of novel (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione analogues have been designed and synthesized in good yields with the objective of selective N-alkylation at thiazolidine 2,4-dione ring in competence with indole ring under basic conditions in the presence of aprotic solvent dimethylformamide (DMF). The newly synthesized compounds have been characterized by spectral data (IR, 1H and 13C NMR, NOE, NOESY, 1H-1H-COSY and LC-MS). Further, molecular docking and ADME studies have revealed that the newly synthesized compounds have very good docking score against antidiabetic and anti-inflammation activities (PPARy and COX-2) as compared with standard rosiglitazone.

中文翻译:

(Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione 类似物的选择性 N-烷基化及其分子对接研究的合成和结构确认

在本研究中,设计并合成了一系列新的 (Z)-5-((5-chloro-1H-indol-3-yl)methylene)thiazolidine-2,4-dione 类似物,目标是在非质子溶剂二甲基甲酰胺 (DMF) 存在下,在碱性条件下,噻唑烷 2,4-二酮环与吲哚环选择性 N-烷基化。新合成的化合物已通过光谱数据(IR、1 H 和13 C NMR、NOE、NOESY、1 H- 1 H-COSY 和 LC-MS)表征。此外,分子对接和 ADME 研究表明,与标准罗格列酮相比,新合成的化合物在抗糖尿病和抗炎活性(PPARγ 和 COX-2)方面具有非常好的对接评分。
更新日期:2021-09-29
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