Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.
Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.
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亚硝基 Diels-Alder 反应衍生的新型白霉素类似物的制备和生物学评价。
DOI：
10.1039/b922450e
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发表时间：
2010
影响因子：
3.2
通讯作者：
Miller,MarvinJ
中科院分区：
文献类型：
--
作者：
Yang,Baiyuan;Zöllner,Tina;Gebhardt,Peter;Möllmann,Ute;Miller,MarvinJ
以白霉素A7为原料，通过亚硝基Diels-Alder反应合成了一系列10，13-二取代16元大环内酯化合物。尽管白霉素具有广泛的组成官能团，但杂环加成反应以高度区域和立体选择性的方式进行。随后还对亚硝基环加合物进行了化学修饰，包括N-O键的还原。大多数白霉素衍生物保留了类似于白霉素A7的抗生素特性，与白霉素本身相反，其中几种具有中等的抗增殖和细胞毒活性。
A series of 10,13-disubstituted 16-membered macrolides was synthesized using nitroso Diels–Alder reactions of leucomycin A7. Despite the extensive constituent functionalities in leucomycin, the hetero cycloaddition reactions proceeded in a highly regio- and stereoselective fashion. Subsequent chemical modifications of the nitroso cycloadducts, including N–O bond reduction, were also conducted. Most leucomycin derivatives retained antibiotic profiles similar to leucomycin A7, and, in contrast to leucomycin itself, several exhibited moderate antiproliferative and cytotoxic activity.