Protecting-Group-Free One-Step Palladium-Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells
作者机构：University of Chinese Academy of SciencesNo.19A Yuquan RoadBejing 100049China State Key Laboratory of Drug ResearchShanghai Institute of Materia MedicaChinese Academy of SciencesShanghai 201203China School of Chinese Materia MedicaNanjing University of Chinese MedicineNanjingJiangsu 210046China Drug Discovery Shandong LaboratoryBohai Rim Advanced Research Institute for Drug DiscoveryYantaiShandong 264117China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2022年第40卷第14期
页 面：1662-1666,I0002页
核心收录：
学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学]
主 题：Natural products Cucurbitacin B Palladium-catalyzed coupling Divergent synthesis Structure-activity relationships
摘 要：The natural product cucurbitacin B has been widely studied because of its multiple biological activities,especially its potent antitumor ***,modifications of cucurbitacin B are mainly focused on the C2 and C16 site,studies on the C25 acetoxy group are still *** successfully developed a palladium-catalyzed allylic coupling of cucurbitacin B with boronic acids,providing a one-step approach to expand the chemical diversity of the C25 *** method was protecting-group-free,showing a good functional group tolerance and a wide substrate scope under mild reaction conditions.A library of 29 derivatives was prepared,compounds 2q and 2u showed higher cytotoxicity against A549 cells than cucurbitacin B,compounds 2n and 2o maintained potency,and the introduced hydroxyl and amino groups could be further derived.
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