Department of Chemistry, Mirpur University of Science and Technology (MUST), 10250 Mirpur, AJK, Pakistan.
Department of Chemistry, Khwaja Fareed University of Engineering & Information Technology, Rahim Yar Khan, 64200, Pakistan.
Z Naturforsch C J Biosci. 2021 Apr 26;76(11-12):467-480. doi: 10.1515/znc-2021-0042. Print 2021 Nov 25.
A series of ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates was synthesized in two steps from thiosemicarbazones (), which were cyclized with ethyl bromopyruvate to ethyl 2-(2-(arylidene)hydrazinyl)thiazole-4-carboxylates . The structures of compounds were established by FT-IR, H- and C-NMR. The structure of compound was confirmed by HRMS. The compounds were then evaluated for their antimicrobial and antioxidant assays. The antioxidant studies revealed, ethyl 2-(2-(4-hydroxy-3-methoxybenzylidene)hydrazinyl)thiazole-4-carboxylate and ethyl 2-(2-(1-phenylethylidene)hydrazinyl)thiazole-4-carboxylate as promising antioxidant agents with %FRSA: 84.46 ± 0.13 and 74.50 ± 0.37, TAC: 269.08 ± 0.92 and 269.11 ± 0.61 and TRP: 272.34 ± 0.87 and 231.11 ± 0.67 μg AAE/mg dry weight of compound. Beside bioactivities, density functional theory (DFT) methods were used to study the electronic structure and properties of synthesized compounds (). The potential of synthesized compounds for possible antiviral targets is also predicted through molecular docking methods. The compounds and showed good binding affinities and inhibition constants to be considered as therapeutic target for M protein of SARS-CoV-2 (COVID-19). The present in-depth analysis of synthesized compounds will put them under the spot light for practical applications as antioxidants and the modification in structural motif may open the way for COVID-19 drug.
从硫代卡巴肼（）出发，经两步反应合成了一系列 2-（2-（芳基亚甲基）肼基）噻唑-4-羧酸乙酯，然后与溴丙酮酸乙酯环化得到 2-（2-（芳基亚甲基）肼基）噻唑-4-羧酸乙酯。通过 FT-IR、H-和 C-NMR 确定了化合物的结构。通过 HRMS 确定了化合物的结构。然后对这些化合物进行了抗菌和抗氧化活性评价。抗氧化研究表明，2-（2-（4-羟基-3-甲氧基苄基亚甲基）肼基）噻唑-4-羧酸乙酯和 2-（2-（1-苯乙基亚甲基）肼基）噻唑-4-羧酸乙酯是具有潜力的抗氧化剂，其 %FRSA 分别为 84.46 ± 0.13 和 74.50 ± 0.37，TAC 分别为 269.08 ± 0.92 和 269.11 ± 0.61，TRP 分别为 272.34 ± 0.87 和 231.11 ± 0.67 μg AAE/mg 化合物干重。除了生物活性外，还使用密度泛函理论（DFT）方法研究了合成化合物的电子结构和性质（）。通过分子对接方法预测了合成化合物作为 SARS-CoV-2（COVID-19）M 蛋白潜在抗病毒靶点的潜力。化合物和显示出良好的结合亲和力和抑制常数，可考虑作为 SARS-CoV-2 M 蛋白的治疗靶点（COVID-19）。对合成化合物的深入分析将使它们成为抗氧化剂的实际应用焦点，并且结构基序的修饰可能为 COVID-19 药物开辟道路。
