{"title":"Synthesis, Characterization and Antibacterial Activity Study of Para-Substituted Derivatives of N-Benzyl-3-Methylbuten-2-Enamides.","authors":"Wenjie Hu, Yinqiu Liu, Jingyi Yu","doi":"10.1002/cbdv.202402088","DOIUrl":null,"url":null,"abstract":"<p><p>In order to deeply explore the effect of para-substituents on the antibacterial activity of N-benzyl-3-methylbuten-2- enamide derivatives, we elaborately synthesized three such para-substituted derivatives (compound a: N-(4-hydroxybenzyl)-3-methylbut-2- enamide; compound b: N-(4-isobutoxybenzyl)-3- methylbut-2-enamide; compound c: N-(4-isopropoxybenzyl) -3-methylbut-2- enamide), of which the structures were determined by ways of single crystal X-ray diffraction data analysis mainly. The antibacterial performance experiments showed that compounds a, b and c were evaluated for their antibacterial (Escherichia coli, Staphylococcus aureus, and Enterobacter aerogenes) activities. Among them, compounds a, b and c have an effective antibacterial reagents for E. coli exhibiting MIC values of 0.01, 0.01 and 0.01 g/mL, respectively, but inactive for E. aerogenes. In addition, compounds b and c have better activity than compound a against S. aureus with MIC values of 0.01 and 0.02 g/mL. These results provide an important basis for further study of the antibacterial properties and structure-activity relationship of these compounds, and are expected to provide valuable reference for the development of new antibacterial drugs.</p>","PeriodicalId":9878,"journal":{"name":"Chemistry & Biodiversity","volume":" ","pages":"e202402088"},"PeriodicalIF":2.3000,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry & Biodiversity","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1002/cbdv.202402088","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
In order to deeply explore the effect of para-substituents on the antibacterial activity of N-benzyl-3-methylbuten-2- enamide derivatives, we elaborately synthesized three such para-substituted derivatives (compound a: N-(4-hydroxybenzyl)-3-methylbut-2- enamide; compound b: N-(4-isobutoxybenzyl)-3- methylbut-2-enamide; compound c: N-(4-isopropoxybenzyl) -3-methylbut-2- enamide), of which the structures were determined by ways of single crystal X-ray diffraction data analysis mainly. The antibacterial performance experiments showed that compounds a, b and c were evaluated for their antibacterial (Escherichia coli, Staphylococcus aureus, and Enterobacter aerogenes) activities. Among them, compounds a, b and c have an effective antibacterial reagents for E. coli exhibiting MIC values of 0.01, 0.01 and 0.01 g/mL, respectively, but inactive for E. aerogenes. In addition, compounds b and c have better activity than compound a against S. aureus with MIC values of 0.01 and 0.02 g/mL. These results provide an important basis for further study of the antibacterial properties and structure-activity relationship of these compounds, and are expected to provide valuable reference for the development of new antibacterial drugs.
为了深入探讨对位取代基对 N-苄基-3-甲基丁烯-2-烯酰胺衍生物抗菌活性的影响,我们精心合成了三种对位取代基衍生物(化合物 a. N-(4-羟基苄基)-3-甲基丁烯-2-烯酰胺;化合物 b. N-(4-异丁氧基苄基)-3-甲基丁烯-2-烯酰胺;化合物 c. N-(4-异丁氧基苄基)-3-甲基丁烯-2-烯酰胺):N-(4-羟基苄基)-3-甲基丁烯-2-烯酰胺;化合物 b:N-(4-异丁氧基苄基)-3-甲基丁烯-2-烯酰胺;化合物 c:N-(4-异丙氧基苄基)-3-甲基丁烯-2-烯酰胺:化合物b:N-(4-异丁氧基苄基)-3-甲基丁-2-烯酰胺;化合物c:N-(4-异丙氧基苄基)-3-甲基丁-2-烯酰胺,其结构主要通过单晶X射线衍射数据分析确定。抗菌性能实验表明,化合物 a、b 和 c 的抗菌(大肠杆菌、金黄色葡萄球菌和产气肠杆菌)活性得到了评价。其中,化合物 a、b 和 c 对大肠杆菌具有有效的抗菌试剂作用,其 MIC 值分别为 0.01、0.01 和 0.01 g/mL,但对产气肠杆菌无活性。此外,化合物 b 和 c 对金黄色葡萄球菌的活性优于化合物 a,其 MIC 值分别为 0.01 和 0.02 克/毫升。这些结果为进一步研究这些化合物的抗菌特性和结构-活性关系提供了重要依据,有望为开发新的抗菌药物提供有价值的参考。
期刊介绍:
Chemistry & Biodiversity serves as a high-quality publishing forum covering a wide range of biorelevant topics for a truly international audience. This journal publishes both field-specific and interdisciplinary contributions on all aspects of biologically relevant chemistry research in the form of full-length original papers, short communications, invited reviews, and commentaries. It covers all research fields straddling the border between the chemical and biological sciences, with the ultimate goal of broadening our understanding of how nature works at a molecular level.
Since 2017, Chemistry & Biodiversity is published in an online-only format.