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Natural scaffolds-inspired synthesis of CF3-substituted macrolides enabled by Rh-catalyzed C-H alkylation macrocyclization

文献类型：期刊论文

作者Bi, Tongyu4,5; Xu, Yi4,5; Xu, Xin3; Tang, Bixi4,5; Yang, Qing4,5; Zang, Yi4,5; Lin, Zhenyang3; Li, Jia1,2,4,5; Yang, Weibo2,4,5
刊名CHINESE CHEMICAL LETTERS
出版日期2022-04-01
卷号33期号:4页码:2015-2020
关键词Rh-catalyzed C-H alkylation Late stage macrocyclization DFT calculation Anti-inflammation
ISSN号1001-8417
DOI10.1016/j.cclet.2021.10.043
通讯作者Lin, Zhenyang(chzlin@ust.hk) ; Li, Jia(jli@simm.ac.cn) ; Yang, Weibo(yweibo@simm.ac.cn)
英文摘要The development of innovative strategies and methods to provide natural product-like macrocycles not accessible by biosynthesis, but endowed with novel bioactivities and simplified structure, is highly desirable. Inspired by the key scaffolds of rapamycin and FR252921, herein, we report a Rh(III)-catalyzed C-H alkylation macrocyclization, which enables access to CF3-substituted macrolides. DFT calculations reveal that the chemoselectivity between C-H alkylation and olefination macrocyclization was highly controllable. Moreover, the unique CF3-substituted macrolides showed potent anti-inflammation activities against TNF-alpha, IL-6 and CCL2 mRNA expression. (C) 2021 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
WOS关键词FLUORESCENS NO. 408813 ; RING-CLOSING METATHESIS ; IMMUNOSUPPRESSANT FK506 ; FR252921 ; FERMENTATION ; DISCOVERY ; RAPAMYCIN
WOS研究方向Chemistry
语种英语
WOS记录号WOS:000789375500053
出版者ELSEVIER SCIENCE INC
源URL[http://119.78.100.183/handle/2S10ELR8/300980]  
专题中国科学院上海药物研究所
通讯作者Lin, Zhenyang; Li, Jia; Yang, Weibo
作者单位1.Pilot Natl Lab Marine Sci & Technol Qingdao, Open Studio Druggabil Res Marine Nat Prod, Qingdao 266237, Peoples R China
2.Univ Chinese Acad Sci, Sch Pharmaceut Sci & Technol, Hangzhou Inst Adv Study, Hangzhou 310024, Peoples R China
3.Hong Kong Univ Sci & Technol, Dept Chem, Hong Kong, Peoples R China
4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
5.Chinese Acad Sci, Key Lab Receptor Res, Shanghai Inst Mat Med SIMM, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Bi, Tongyu,Xu, Yi,Xu, Xin,et al. Natural scaffolds-inspired synthesis of CF3-substituted macrolides enabled by Rh-catalyzed C-H alkylation macrocyclization[J]. CHINESE CHEMICAL LETTERS,2022,33(4):2015-2020.
APA Bi, Tongyu.,Xu, Yi.,Xu, Xin.,Tang, Bixi.,Yang, Qing.,...&Yang, Weibo.(2022).Natural scaffolds-inspired synthesis of CF3-substituted macrolides enabled by Rh-catalyzed C-H alkylation macrocyclization.CHINESE CHEMICAL LETTERS,33(4),2015-2020.
MLA Bi, Tongyu,et al."Natural scaffolds-inspired synthesis of CF3-substituted macrolides enabled by Rh-catalyzed C-H alkylation macrocyclization".CHINESE CHEMICAL LETTERS 33.4(2022):2015-2020.

入库方式： OAI收割

来源：上海药物研究所

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