Synthesis and biological evaluation of some heterocyclic scaffolds based on the multifunctional N‐(4‐acetylphenyl)‐2‐chloroacetamide,Journal of Heterocyclic Chemistry

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Synthesis and biological evaluation of some heterocyclic scaffolds based on the multifunctional N‐(4‐acetylphenyl)‐2‐chloroacetamide
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-05-25 , DOI: 10.1002/jhet.4012
Ehab Abdel‐Latif ₁ , Mustafa M. Fahad ₁ , Amr El‐Demerdash ₁ , Mohamed A. Ismail ₁

Affiliation

The chloroacetamide derivative, 1 , was used as a versatile precursor for the synthesis of various types of N ‐aryl‐2‐(benzothiazol‐2‐ylthio)acetamide derivatives. The reaction of 1 with 2‐mercaptobenzothiazole followed by condensation reaction of the produced sulfide with phenylhydrazine, 2‐cyanoacetohydrazide, and/or thiosemicarbazide furnished the conforming condensation products, 4 , 7 , and 10 , respectively. Treatment of the phenylhydrazone product, 4 , with Vilsmeier formylation reagent (POCl₃/DMF) yielded the corresponding 4‐formylpyrazole derivative, 5 . The thiosemicarbazone product, 10 , was reacted with ethyl bromoacetate to furnish the thiazolin‐4‐one derivative, 11 . The substitution reactions of chloroacetamide derivative, 1 , with 2‐mercapto‐4,6‐dimethylnicotinonitrile and 6‐amino‐2‐mercaptopyrimidin‐4‐ol, were explored to identify the sulfide products, 14 and 17 . Cyclization of 14 into its corresponding thieno[2,3‐b ]pyridine compound, 15 , was performed using sodium ethoxide. The thiosemicarbazone, 10 , and sulfide derivative, 14 , were found to be the most potent antibacterial compounds against Escherichia coli and Staphylococcus aureus , exhibiting growth inhibitory activities of 80.8% and 91.7%, respectively. Moreover, the thiosemicarbazone, 10 , displayed the most significant antioxidant activity with inhibitory activity of 82.6%, which comes close to the antioxidant activity of L‐ascorbic acid.

中文翻译：

基于多功能N-（4-乙酰苯基）-2-氯乙酰胺的一些杂环支架的合成和生物学评估

氯乙酰胺衍生物1被用作合成各种类型的N-芳基-2-（苯并噻唑-2-基硫基）乙酰胺衍生物的通用前体。的反应1与2-巯基苯并接着用苯肼，2- cyanoacetohydrazide所产生的硫化物的缩合反应，和/或氨基硫脲提供的符合缩合产物，4，7，和10，分别。用Vilsmeier甲酰化试剂（POCl ₃ / DMF）处理苯hydr产物4，得到相应的4-甲酰基吡唑衍生物5。硫半脲产品，10与溴乙酸乙酯反应，得到噻唑啉-4-酮衍生物11。探索了氯乙酰胺衍生物1与2-巯基4,4,6-二甲基烟腈和6-氨基-2-巯基嘧啶丁-4-醇的取代反应，以鉴定硫化物产物14和17。使用乙醇钠将14环化为其相应的噻吩并[2,3- b ]吡啶化合物15。已发现10硫代半碳杂14和14的硫化物衍生物是对大肠杆菌和细菌最有效的抗菌化合物。金黄色葡萄球菌的生长抑制活性分别为80.8％和91.7％。此外，硫半脲10表现出最显着的抗氧化活性，抑制活性为82.6％，接近L-抗坏血酸的抗氧化活性。

更新日期：2020-05-25

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