马文霉素 A 及其结构类似物胞嘧啶 C 的全合成及其对分枝杆菌和细胞内分枝杆菌抗菌活性的评估

IF 2.1 3区 化学 Q2 CHEMISTRY, ORGANIC
Hanaka Satoh , Daiki Lee , Shiho Arima , Kanji Hosoda , Satoru Shigeno , Hiroshi Tomoda , Taichi Ohshiro , Tohru Nagamitsu
{"title":"马文霉素 A 及其结构类似物胞嘧啶 C 的全合成及其对分枝杆菌和细胞内分枝杆菌抗菌活性的评估","authors":"Hanaka Satoh ,&nbsp;Daiki Lee ,&nbsp;Shiho Arima ,&nbsp;Kanji Hosoda ,&nbsp;Satoru Shigeno ,&nbsp;Hiroshi Tomoda ,&nbsp;Taichi Ohshiro ,&nbsp;Tohru Nagamitsu","doi":"10.1016/j.tet.2024.134299","DOIUrl":null,"url":null,"abstract":"<div><div>Mavintramycin A is a new aminohexopyranose nucleoside antibiotic with potent anti-<em>Mycobacterium avium</em> complex (MAC) activity against <em>M. avium</em> and <em>M. intracellulare</em>. Herein, we report the total syntheses of mavintramycin A and its structural analog cytosaminomycin C, which is a known anticoccidial antibiotic. Furthermore, the anti-MAC activities of mavintramycin A, cytosaminomycin C, and their corresponding <em>p</em>-methoxybenzyl-protected analogs were evaluated. Notably, the developed synthetic route enables ready access to various analogs of mavintramycin A for structure-activity relationship studies.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"168 ","pages":"Article 134299"},"PeriodicalIF":2.1000,"publicationDate":"2024-10-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Total syntheses of mavintramycin A and its structural analog, cytosaminomycin C, and evaluation of their antibacterial activities against Mycobacterium avium and Mycobacterium intracellulare\",\"authors\":\"Hanaka Satoh ,&nbsp;Daiki Lee ,&nbsp;Shiho Arima ,&nbsp;Kanji Hosoda ,&nbsp;Satoru Shigeno ,&nbsp;Hiroshi Tomoda ,&nbsp;Taichi Ohshiro ,&nbsp;Tohru Nagamitsu\",\"doi\":\"10.1016/j.tet.2024.134299\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Mavintramycin A is a new aminohexopyranose nucleoside antibiotic with potent anti-<em>Mycobacterium avium</em> complex (MAC) activity against <em>M. avium</em> and <em>M. intracellulare</em>. Herein, we report the total syntheses of mavintramycin A and its structural analog cytosaminomycin C, which is a known anticoccidial antibiotic. Furthermore, the anti-MAC activities of mavintramycin A, cytosaminomycin C, and their corresponding <em>p</em>-methoxybenzyl-protected analogs were evaluated. Notably, the developed synthetic route enables ready access to various analogs of mavintramycin A for structure-activity relationship studies.</div></div>\",\"PeriodicalId\":437,\"journal\":{\"name\":\"Tetrahedron\",\"volume\":\"168 \",\"pages\":\"Article 134299\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-10-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040402024004800\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040402024004800","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

马文曲霉素 A 是一种新的氨基己吡喃糖核苷类抗生素,对阿维菌素分枝杆菌和细胞内分枝杆菌具有很强的抗分枝杆菌复合体(MAC)活性。在此,我们报告了马文曲霉素 A 及其结构类似物胞嘧啶霉素 C 的全合成,后者是一种已知的抗球菌抗生素。此外,我们还评估了马文曲霉素 A、胞氨霉素 C 及其相应的对甲氧基苄基保护类似物的抗 MAC 活性。值得注意的是,所开发的合成路线可随时获得各种马文霉素 A 类似物,用于结构-活性关系研究。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Total syntheses of mavintramycin A and its structural analog, cytosaminomycin C, and evaluation of their antibacterial activities against Mycobacterium avium and Mycobacterium intracellulare

Total syntheses of mavintramycin A and its structural analog, cytosaminomycin C, and evaluation of their antibacterial activities against Mycobacterium avium and Mycobacterium intracellulare
Mavintramycin A is a new aminohexopyranose nucleoside antibiotic with potent anti-Mycobacterium avium complex (MAC) activity against M. avium and M. intracellulare. Herein, we report the total syntheses of mavintramycin A and its structural analog cytosaminomycin C, which is a known anticoccidial antibiotic. Furthermore, the anti-MAC activities of mavintramycin A, cytosaminomycin C, and their corresponding p-methoxybenzyl-protected analogs were evaluated. Notably, the developed synthetic route enables ready access to various analogs of mavintramycin A for structure-activity relationship studies.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Tetrahedron
Tetrahedron 化学-有机化学
CiteScore
3.90
自引率
4.80%
发文量
439
审稿时长
34 days
期刊介绍: Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.
×
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
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
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 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信