{"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 , Daiki Lee , Shiho Arima , Kanji Hosoda , Satoru Shigeno , Hiroshi Tomoda , Taichi Ohshiro , 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 , Daiki Lee , Shiho Arima , Kanji Hosoda , Satoru Shigeno , Hiroshi Tomoda , Taichi Ohshiro , 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。
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.
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.
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