新型来源于亚硝胺 Diels-Alder 反应的莱菔素类似物的制备和生物学评价。
Preparation and biological evaluation of novel leucomycin analogs derived from nitroso Diels-Alder reactions.
机构信息
Department of Chemistry and Biochemistry, University of Notre Dame, 251 Nieuwland ScienceHall, Notre Dame, Indiana 46556, USA.
出版信息
Org Biomol Chem. 2010 Feb 7;8(3):691-7. doi: 10.1039/b922450e. Epub 2009 Dec 11.
Abstract
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.
摘要
使用利福霉素 A7 的亚硝酮 Diels-Alder 反应，合成了一系列 10,13-二取代的 16 元大环内酯。尽管利福霉素中存在广泛的组成官能团，但杂环加成反应仍以高度区域和立体选择性的方式进行。随后对亚硝酮环加成产物进行了化学修饰，包括 N-O 键还原。大多数利福霉素衍生物保留了与利福霉素 A7 相似的抗生素特性，与利福霉素本身不同，几种具有中等的抗增殖和细胞毒性活性。
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