Protecting-Group-Free One-Step Palladium-Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells
文献类型：期刊论文
| 作者 | Zhuo, Ning3,4; Ma, Jie3; Cao, Lei2,3; Chen, Linhai3 ; Nan, Fajun1,3,4
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| 刊名 | CHINESE JOURNAL OF CHEMISTRY
 |
| 出版日期 | 2022-05-13 |
| 页码 | 5 |
| 关键词 | Natural products Cucurbitacin B Palladium-catalyzed couplingl Divergent synthesis Structure-activity relationships |
| ISSN号 | 1001-604X |
| DOI | 10.1002/cjoc.202200106 |
| 通讯作者 | Nan, Fajun(fjnan@simm.ac.cn) |
| 英文摘要 | Comprehensive Summary The natural product cucurbitacin B has been widely studied because of its multiple biological activities, especially its potent antitumor effects. However, modifications of cucurbitacin B are mainly focused on the C2 and C16 site, studies on the C25 acetoxy group are still limited. We 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 position. Our 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. |
| WOS关键词 | TRITERPENOIDS ; GROWTH ; MICE ; L. |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000794258800001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/300974]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Nan, Fajun |
| 作者单位 | 1.Bohai Rim Adv Res Inst Drug Discovery, Drug Discovery Shandong Lab, Yantai 264117, Shandong, Peoples R China 2.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210046, Jiangsu, Peoples R China 3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China 4.Univ Chinese Acad Sci, 19A Yuquan Rd, Beijing 100049, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhuo, Ning,Ma, Jie,Cao, Lei,et al. Protecting-Group-Free One-Step Palladium-Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells[J]. CHINESE JOURNAL OF CHEMISTRY,2022:5. |
| APA | Zhuo, Ning,Ma, Jie,Cao, Lei,Chen, Linhai,&Nan, Fajun.(2022).Protecting-Group-Free One-Step Palladium-Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells.CHINESE JOURNAL OF CHEMISTRY,5. |
| MLA | Zhuo, Ning,et al."Protecting-Group-Free One-Step Palladium-Catalyzed Coupling on C25 of Cucurbitacin B Expands Chemical Diversity with Improved Cytotoxicity against A549 Cells".CHINESE JOURNAL OF CHEMISTRY (2022):5. |
入库方式： OAI收割
来源：上海药物研究所
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