Synthesis, in vitro acetylcholinesterase, butyrylcholinesterase activities and molecular docking study of 1,3-oxathiol-2-imine derivatives

IF 2.218 Q2 Chemistry Chemical Data Collections Pub Date : 2024-01-18 DOI:10.1016/j.cdc.2024.101120

Hayat Ullah , Muhammad Nabi , Maliha Sarfraz , Fahad Khan , Muhammad Saleem Khan , Rabia Khan , Mehboob Khan , Muhammed Perviaz , Fazal Rahim

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Abstract

We have synthesized eleven derivatives of 1,3-oxathio-2-imine, characterized through NMR, HREI-MS and evaluated against acetylcholinesterase and butyrylcholinesterase enzymes. All synthesized derivative showed good inhibitory potential, having IC₅₀ value ranged from 1.10 ± 0.05 to 23.20 ± 0.40 µM (AChE) and 2.30 ± 0.10 to 32.00 ± 0.80 µM (BuChE) as compare to standard drug Donepzil (IC₅₀ = 2.16 ± 0.12 & 4.5 ± 0.11 µM, respectively). In both case, derivative 7 (IC₅₀ = 1.10 ± 0.05 µM & 2.30 ± 0.10 µM, respectively) was found the most potent among the series. Structure activity relationship was carried out which mainly depend upon the nature, position, number and electron donating/withdrawing effect of the substituent/s on phenyl ring. Molecular docking was carried out to determine the binding attraction of the most potent derivatives with the active site of enzymes.

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1,3-oxathiol-2-imine 衍生物的合成、体外乙酰胆碱酯酶和丁酰胆碱酯酶活性及分子对接研究

我们合成了 11 种 1,3-oxathio-2-imine 衍生物，通过核磁共振和 HREI-MS 对其进行了表征，并对乙酰胆碱酯酶和丁酰胆碱酯酶进行了评估。与标准药物多奈哌齐（IC50 = 2.16 ± 0.12 & 4.5 ± 0.11 µM）相比，所有合成的衍生物都表现出良好的抑制潜力，IC50 值分别为 1.10 ± 0.05 至 23.20 ± 0.40 µM（乙酰胆碱酯酶）和 2.30 ± 0.10 至 32.00 ± 0.80 µM（丁酰胆碱酯酶）。在这两种情况下，衍生物 7（IC50 = 1.10 ± 0.05 µM & 2.30 ± 0.10 µM，分别为 1.10 ± 0.05 µM & 2.30 ± 0.10 µM）被认为是该系列中最有效的。结构活性关系主要取决于苯环上取代基的性质、位置、数量和电子供/吸效应。进行了分子对接，以确定最有效的衍生物与酶活性位点的结合吸引力。

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来源期刊

Chemical Data Collections Chemistry-Chemistry (all)

CiteScore

6.10

自引率

0.00%

发文量

169

审稿时长

24 days

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