An Efficient Catalyst-Free One-Pot Synthesis and In Vitro Biological Activity Evaluation of Novel Isoquinoline Derivatives of Fatty Acids

IF 0.8 4区 医学 Q4 CHEMISTRY, MEDICINAL Pharmaceutical Chemistry Journal Pub Date : 2024-08-06 DOI:10.1007/s11094-024-03189-9
Razieh Rahimizadeh, Akbar Mobinikhaledi, Hassan Moghanian, Mahta Mobinikhaledi, Seyedeh sara Kashaninejad
{"title":"An Efficient Catalyst-Free One-Pot Synthesis and In Vitro Biological Activity Evaluation of Novel Isoquinoline Derivatives of Fatty Acids","authors":"Razieh Rahimizadeh, Akbar Mobinikhaledi, Hassan Moghanian, Mahta Mobinikhaledi, Seyedeh sara Kashaninejad","doi":"10.1007/s11094-024-03189-9","DOIUrl":null,"url":null,"abstract":"<p>There is good evidence that fatty acid derivatives have antibacterial activity and represent a promising approach to developing the next generation of antibacterial agents. In the present work, some new isoquinolin derivatives were synthesized via the Betti reaction. Three-component reaction of aryl aldehydes, 2,7-naphthalenediol and ammonium carboxylate of fatty acids with different chains in EtOH under reflux conditions offered related isoquinolin compounds in good to excellent yields. Some advantages of this procedure are short reaction times, free catalyst, high yield of products and easy work-up. The structure of synthesized compounds was characterized by IR, <sup>1</sup>H, and <sup>13</sup>C NMR data as well as microanalysis results. In addition, these novel materials were evaluated for their biological activities against <i>Staphylococcus aureus</i> (ATCC 25923) and <i>Escherichia coli</i> (ATCC 25922) bacteria. The obtained data confirm that isoquinolin derivatives <b>4c</b>, <b>4e</b>, <b>4f</b>, <b>4g</b>, <b>4m</b>, <b>4n</b>, <b>4p</b>, <b>4q</b> exert excellent antimicrobial activity against these tested bacterial strains.</p>","PeriodicalId":19990,"journal":{"name":"Pharmaceutical Chemistry Journal","volume":null,"pages":null},"PeriodicalIF":0.8000,"publicationDate":"2024-08-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Pharmaceutical Chemistry Journal","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1007/s11094-024-03189-9","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0

Abstract

There is good evidence that fatty acid derivatives have antibacterial activity and represent a promising approach to developing the next generation of antibacterial agents. In the present work, some new isoquinolin derivatives were synthesized via the Betti reaction. Three-component reaction of aryl aldehydes, 2,7-naphthalenediol and ammonium carboxylate of fatty acids with different chains in EtOH under reflux conditions offered related isoquinolin compounds in good to excellent yields. Some advantages of this procedure are short reaction times, free catalyst, high yield of products and easy work-up. The structure of synthesized compounds was characterized by IR, 1H, and 13C NMR data as well as microanalysis results. In addition, these novel materials were evaluated for their biological activities against Staphylococcus aureus (ATCC 25923) and Escherichia coli (ATCC 25922) bacteria. The obtained data confirm that isoquinolin derivatives 4c, 4e, 4f, 4g, 4m, 4n, 4p, 4q exert excellent antimicrobial activity against these tested bacterial strains.

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
新型脂肪酸异喹啉衍生物的高效无催化剂一锅合成及体外生物活性评估
有充分证据表明,脂肪酸衍生物具有抗菌活性,是开发下一代抗菌剂的一种很有前途的方法。本研究通过 Betti 反应合成了一些新的异喹啉衍生物。在回流条件下,芳基醛、2,7-萘二醇和不同链脂肪酸的羧酸铵在 EtOH 中发生三组分反应,生成了相关的异喹啉化合物,收率从良好到极佳。该方法的一些优点是反应时间短、无需催化剂、产品收率高且易于加工。通过红外光谱、1H 和 13C NMR 数据以及显微分析结果对合成化合物的结构进行了表征。此外,还评估了这些新型材料对金黄色葡萄球菌(ATCC 25923)和大肠杆菌(ATCC 25922)的生物活性。所得数据证实,异喹啉衍生物 4c、4e、4f、4g、4m、4n、4p、4q 对这些受试细菌菌株具有极佳的抗菌活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Pharmaceutical Chemistry Journal
Pharmaceutical Chemistry Journal CHEMISTRY, MEDICINAL-PHARMACOLOGY & PHARMACY
CiteScore
1.30
自引率
22.20%
发文量
226
审稿时长
3-8 weeks
期刊介绍: Pharmaceutical Chemistry Journal is a monthly publication devoted to scientific and technical research on the creation of new drugs and the improvement of manufacturing technology of drugs and intermediates. International contributors cover the entire spectrum of new drug research, including: methods of synthesis; results of pharmacological, toxicological, and biochemical studies; investigation of structure - activity relationships in prediction of new compounds; methods and technical facilities used; and problems associated with the development of ecologically safe and economically feasible methods of industrial production. In addition, analytical reviews of the international literature in the field provide coverage of the most recent developments around the world. Pharmaceutical Chemistry Journal is a translation of the Russian journal Khimiko-Farmatsevticheskii Zhurnal. The Russian Volume Year is published in English from April. All articles are peer-reviewed.
期刊最新文献
Antiproliferative Activity Compounds Isolated from the Marine Fungus Penicillium terrigenum Modern Approaches to Mathematical Modeling of the Process of Direct Pressing of Tablets Validated UV-Spectrophotometric Method for Pirfenidone Estimation in Bulk Drug, Marketed Tablet, and Nanoparticle Formulation Determination of the Rosmarinic Acid Content in Mentha piperita L. Leaves by HPLC Synthesis of Acetaminophen Under Microwave Irradiation in the Presence of H-Clinoptilolite
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1