Synthesis, antidiabetic activity and molecular docking studies of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles

IF 3.9 2区化学 Q2 CHEMISTRY, APPLIED

Molecular Diversity Pub Date : 2023-06-16 DOI:10.1007/s11030-023-10674-y

Nagesh Patnam, Kishan Chevula, Prasad Chennamsetti, Balaswamy Aleti, Aruna Kumari Kotha, Vijjulatha Manga

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Abstract

A series of novel aryl benzylidenethiazolidine-2,4-dione based 1,2,3-triazoles synthesized in a straightforward route consisting of benzylidenethiazolidine-2,4-dione and 1,2,3-triazole pharmacophores. The new scaffolds tested for in vitro antidiabetic activity by inhibition of aldose reductase enzyme and its inhibition measured in half of Inhibition Concentration (IC₅₀). The activity results correlated with standard reference Sorbinil (IC₅₀: 3.45 ± 0.25 µM). Among all the titled compounds 8f (1.42 ± 0.21 µM), 8d (1.85 ± 0.39 µM), 13a (1.94 ± 0.27 µM) and 8b (1.98 ± 0.58 µM) shown potent activity. In addition, molecular docking results against the crystal structure of aldose reductase (PDB ID: 1PWM) revealed that the binding affinities shown by all synthesized compounds are higher than the reference compound Sorbinil. The docking scores, H-bond interactions, and hydrophobic interactions well defined inhibition strength of all compounds.

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新型芳基亚苄基噻唑烷-2,4-二酮基 1,2,3-三唑的合成、抗糖尿病活性和分子对接研究。

以苄基亚噻唑烷-2,4-二酮和 1,2,3- 三唑药基为基础，通过简单的方法合成了一系列新型芳基苄基亚噻唑烷-2,4-二酮基 1,2,3- 三唑。新支架通过抑制醛糖还原酶进行了体外抗糖尿病活性测试，其抑制作用以抑制浓度的一半（IC50）来衡量。活性结果与标准参考物索比尼尔（IC50：3.45 ± 0.25 µM）相关。在所有标题化合物中，8f（1.42 ± 0.21 µM）、8d（1.85 ± 0.39 µM）、13a（1.94 ± 0.27 µM）和 8b（1.98 ± 0.58 µM）显示出强大的活性。此外，与醛糖还原酶晶体结构（PDB ID：1PWM）的分子对接结果显示，所有合成化合物的结合亲和力均高于参考化合物索比尼尔。对接得分、氢键相互作用和疏水相互作用很好地确定了所有化合物的抑制强度。

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来源期刊

Molecular Diversity 化学-化学综合

CiteScore

7.30

自引率

7.90%

发文量

219

审稿时长

2.7 months

期刊介绍： Molecular Diversity is a new publication forum for the rapid publication of refereed papers dedicated to describing the development, application and theory of molecular diversity and combinatorial chemistry in basic and applied research and drug discovery. The journal publishes both short and full papers, perspectives, news and reviews dealing with all aspects of the generation of molecular diversity, application of diversity for screening against alternative targets of all types (biological, biophysical, technological), analysis of results obtained and their application in various scientific disciplines/approaches including: combinatorial chemistry and parallel synthesis; small molecule libraries; microwave synthesis; flow synthesis; fluorous synthesis; diversity oriented synthesis (DOS); nanoreactors; click chemistry; multiplex technologies; fragment- and ligand-based design; structure/function/SAR; computational chemistry and molecular design; chemoinformatics; screening techniques and screening interfaces; analytical and purification methods; robotics, automation and miniaturization; targeted libraries; display libraries; peptides and peptoids; proteins; oligonucleotides; carbohydrates; natural diversity; new methods of library formulation and deconvolution; directed evolution, origin of life and recombination; search techniques, landscapes, random chemistry and more;