A novel cyclobutane-derived thiazole–thiourea hybrid with a potency against COVID-19 and tick-borne encephalitis: synthesis, characterization, and computational analysis

IF 2.1 3区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Journal of Sulfur Chemistry Pub Date : 2024-01-01 DOI:10.1080/17415993.2023.2260918

Rebaz Anwar Omar , Pelin Koparir , Metin Koparir , Damir A. Safin

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引用次数: 0

Abstract

In the present contribution, a novel cyclobutane-derived thiazole–thiourea hybrid 1-(4-(3-methyl-3-phenylcyclobutyl)thiazol-2-yl)−3-(p-tolyl)thiourea (1), which was readily fabricated from addition of p-isothiocyanatotoluene to 4-(3-methyl-3-phenylcyclobutyl)thiazol-2-amine, is reported. The formation of 1 was firmly confirmed by the means of elemental analysis, and IR and ¹H NMR spectroscopy. Theoretical DFT-based computations were additionally applied to reveal the structure and electronic features of the title compound. The chemical activity of 1 was estimated by the reactivity descriptors and MEP surface. ADMET properties of the reported compound were predicted in silico using online services. Potential inhibition of a series of the SARS-CoV-2 and tick-borne encephalitis proteins by 1 was studied using molecular docking, which, in turn, allowed to reveal the ligand efficiency scores for the resulting protein–1 complexes. It was established that 1 exhibits the best inhibition activity against Nonstructural protein 14 (N7-MTase) and tick-borne encephalitis virus (TBEV) glycoprotein amongst the studied SARS-CoV-2 and TBE proteins, respectively.

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一种新型环丁烷衍生噻唑-硫脲混合物，对 COVID-19 和蜱传脑炎有特效：合成、表征和计算分析

本论文报告了一种新型环丁烷衍生噻唑-硫脲混合物 1-(4-(3-甲基-3-苯基环丁基)噻唑-2-基)-3-(对甲苯基)硫脲 (1)，它是由对异硫氰基甲苯与 4-(3-甲基-3-苯基环丁基)噻唑-2-胺相加而轻易制成的。通过元素分析、红外光谱和 1H NMR 光谱，1 的形成得到了证实。此外，还应用了基于 DFT 的理论计算来揭示标题化合物的结构和电子特征。通过反应性描述符和 MEP 表面估算了 1 的化学活性。利用在线服务对报告化合物的 ADMET 特性进行了硅预测。利用分子对接法研究了 1 对一系列 SARS-CoV-2 和蜱传脑炎蛋白的潜在抑制作用，进而揭示了由此产生的蛋白-1 复合物的配体效率得分。结果表明，在所研究的 SARS-CoV-2 和 TBE 蛋白中，1 对非结构蛋白 14（N7-MTase）和蜱传脑炎病毒（TBEV）糖蛋白的抑制活性最好。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Sulfur Chemistry CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

4.10

自引率

9.10%

发文量

审稿时长

6-12 weeks

期刊介绍： The Journal of Sulfur Chemistry is an international journal for the dissemination of scientific results in the rapidly expanding realm of sulfur chemistry. The journal publishes high quality reviews, full papers and communications in the following areas: organic and inorganic chemistry, industrial chemistry, materials and polymer chemistry, biological chemistry and interdisciplinary studies directly related to sulfur science. Papers outlining theoretical, physical, mechanistic or synthetic studies pertaining to sulfur chemistry are welcome. Hence the target audience is made up of academic and industrial chemists with peripheral or focused interests in sulfur chemistry. Manuscripts that truly define the aims of the journal include, but are not limited to, those that offer: a) innovative use of sulfur reagents; b) new synthetic approaches to sulfur-containing biomolecules, materials or organic and organometallic compounds; c) theoretical and physical studies that facilitate the understanding of sulfur structure, bonding or reactivity; d) catalytic, selective, synthetically useful or noteworthy transformations of sulfur containing molecules; e) industrial applications of sulfur chemistry; f) unique sulfur atom or molecule involvement in interfacial phenomena; g) descriptions of solid phase or combinatorial methods involving sulfur containing substrates. Submissions pertaining to related atoms such as selenium and tellurium are also welcome. Articles offering routine heterocycle formation through established reactions of sulfur containing substrates are outside the scope of the journal.