Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents.

International Journal of Medicinal Chemistry Pub Date : 2018-10-16 eCollection Date: 2018-01-01 DOI:10.1155/2018/5758076
Grady L Nelson, Michael J Williams, Shirisha Jonnalagadda, Mohammad A Alam, Gautam Mereddy, Joseph L Johnson, Sravan K Jonnalagadda
{"title":"Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents.","authors":"Grady L Nelson,&nbsp;Michael J Williams,&nbsp;Shirisha Jonnalagadda,&nbsp;Mohammad A Alam,&nbsp;Gautam Mereddy,&nbsp;Joseph L Johnson,&nbsp;Sravan K Jonnalagadda","doi":"10.1155/2018/5758076","DOIUrl":null,"url":null,"abstract":"<p><p>Allylic acetates derived from Baylis-Hillman reaction undergo efficient nucleophilic isomerization with imidazoles and triazoles to provide imidazolylmethyl and triazolylmethyl cinnamates stereoselectively. Antifungal evaluation of these derivatives against <i>Cryptococcus neoformans</i> exhibits good minimum inhibitory concentration values. These compounds exhibit low toxicity in proliferating MCF-7 breast cancer cell line. Structure activity relationship studies indicate that halogenated aromatic derivatives provide better antifungal activity.</p>","PeriodicalId":14082,"journal":{"name":"International Journal of Medicinal Chemistry","volume":"2018 ","pages":"5758076"},"PeriodicalIF":0.0000,"publicationDate":"2018-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1155/2018/5758076","citationCount":"1","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"International Journal of Medicinal Chemistry","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1155/2018/5758076","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2018/1/1 0:00:00","PubModel":"eCollection","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 1

Abstract

Allylic acetates derived from Baylis-Hillman reaction undergo efficient nucleophilic isomerization with imidazoles and triazoles to provide imidazolylmethyl and triazolylmethyl cinnamates stereoselectively. Antifungal evaluation of these derivatives against Cryptococcus neoformans exhibits good minimum inhibitory concentration values. These compounds exhibit low toxicity in proliferating MCF-7 breast cancer cell line. Structure activity relationship studies indicate that halogenated aromatic derivatives provide better antifungal activity.

Abstract Image

Abstract Image

Abstract Image

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
Baylis-Hillman反应衍生咪唑和三唑肉桂酸酯的合成与评价。
由Baylis-Hillman反应得到的烯丙酸酯与咪唑和三唑进行了高效的亲核异构化反应,得到立体选择性咪唑甲基肉桂酸酯和三唑甲基肉桂酸酯。这些衍生物对新型隐球菌的抗真菌评价显示出良好的最小抑制浓度值。这些化合物对增殖的MCF-7乳腺癌细胞系表现出低毒性。构效关系研究表明,卤代芳香衍生物具有较好的抗真菌活性。
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
自引率
0.00%
发文量
0
期刊介绍: International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis. International Journal of Medicinal Chemistry is a peer-reviewed, Open Access journal that publishes original research articles as well as review articles in all areas of chemistry associated with drug discovery, design, and synthesis.
期刊最新文献
Hair Growth Promoting Effect of Dicerocaryum senecioides Phytochemicals. Caffeates and Caffeamides: Synthetic Methodologies and Their Antioxidant Properties Evaluation of the Molecular State of Piperine in Cyclodextrin Complexes by Near-Infrared Spectroscopy and Solid-State Fluorescence Measurements. Synthesis and Evaluation of Baylis-Hillman Reaction Derived Imidazole and Triazole Cinnamates as Antifungal Agents. Crystallography and Its Impact on Carbonic Anhydrase Research.
×
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