Novel desosamine-modified 14- and 15-membered macrolides without antibacterial activity

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• 作者：Ivana Palej Jakopovi膰^a ; ^&dagger ; ; Mirjana Bukvi膰 Kraja膷i膰^a ; ^&dagger ; ; Maja Matanovi膰 &Scaron ; kugor^a ; ^&dagger ; ; Vlado &Scaron ; timac^a ; ^&dagger ; ; Dijana Pe&scaron ; i膰^a ; ^&dagger ; ; Ines Vujasinovi膰^a ; ^&dagger ; ; Sulejman Alihod啪i膰^a ; ^&dagger ; ; Hana 膶ip膷i膰 Paljetak^b ; Goran Kragol^a ; ^&dagger ; ; ^{goran.kragol@glpg.com}
• 关键词：Macrolide ; 1 ; 3-Oxazolidin-2-one ; N-alkylations ; Antibacterial activity
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2012
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：15 May, 2012
• 卷：22
• 期：10
• 页码：3527-3530
• 文件大小：484 K

摘要

Novel modifications of the desosamine sugar of 14- and 15-membered antibacterial macrolides, in which the desosamine was fused with N-substituted-1,3-oxazolidin-2-ones, were developed in order to completely suppress antibacterial activity and make them promising agents for other biological targets. The synthesis of such bicyclic desosamine derivatives, especially 1,3-oxazolidin-2-one formation, was optimized and conducted under mild conditions without a need for protection/deprotection steps for other functional groups. A focused series of novel desosamine-modified macrolide derivatives was prepared and their antibacterial activities tested. It was shown that these macrolide derivatives do not possess any residual antibacterial activity.