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Asymmetric macrocyclization enabled by Rh(III)-catalyzed C-H activation: Enantioenriched macrocyclic inhibitor of Zika virus infection

文献类型：期刊论文

作者Chen, Chao5,6,7; Yu, Wenwen6; Huang, Guangen4; Ren, Xuelian3; Chen, Xiangli4; Li, Yixin7; Liang, Shenggui7; Xu, Mengmeng4; Zheng, Mingyue6,7; Yang, Yaxi2,5,6,7
刊名CHINESE CHEMICAL LETTERS
出版日期2024-11-01
卷号35期号:11页码:6
关键词C -H activation Carboamidation Enantioselective macrocyclization Anti-Zika virus activity
ISSN号1001-8417
DOI10.1016/j.cclet.2024.109574
通讯作者Yang, Yaxi(yangyaxi@simm.ac.cn) ; Huang, He(hhuang@simm.ac.cn) ; Tang, Wei(tangwei@simm.ac.cn) ; Zhou, Bing(zhoubing@simm.ac.cn)
英文摘要The development of enantioselective C-H macrocyclizations to efficiently access structurally diversified macrocycles is highly desirable, but remain a big challenge. Herein, we reported the first rhodium(III)catalyzed asymmetric intramolecular C-H macrocyclization, enabling the efficient synthesis of structurally diverse enantioenriched macrocycles. This robust enantioselective C-H macrocyclization has a broad functional group tolerance, excellent enantioselectivities (up to 98.5:1.5 e.r.) and a mild reaction condition, releasing CO2 2 as the single by-product. More significantly, the resulting unique enantioenriched 19-membered macrocycle 2f was found to demonstrate a potent in vitro anti-Zika virus (ZIKV) activity without obvious cytotoxicity. Further investigation revealed that the anti-ZIKV activity is presumably attributed to an autophagy inhibition in the early stage of viral infection by down-regulating the expression of autophagy related gene Atg12. (c) 2024 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RING-CLOSING METATHESIS ; CARBOAMINATION REACTIONS ; ALKENES ; MACROLACTONIZATION ; FUNCTIONALIZATION ; CATALYSIS ; LIGANDS ; BONDS
资助项目National Natural Science Founda-tion of China[81973166] ; Science and Technology Commission of Shanghai Municipality[22XD1424600] ; Natural Science Foundation of Shanghai Municipality[22ZR1474100] ; Taishan Scholar Foundation of Shandong Province[tsqn202306322] ; National Key R&D Program of China[2021YFC230 070 0] ; Shandong Laboratory Program[SYS202205] ; Shandong Provincial Natural Science Foundation[ZR2023LSW003] ; Shandong Provincial Natural Science Foundation[ZR2023JQ028]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001286108100001
出版者ELSEVIER SCIENCE INC
源URL[http://119.78.100.183/handle/2S10ELR8/312706]  
专题新药研究国家重点实验室
通讯作者Yang, Yaxi; Huang, He; Tang, Wei; Zhou, Bing
作者单位1.Fudan Univ, Sch Pharm, Dept Med Chem, Shanghai 201203, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China
4.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
5.Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Peoples R China
6.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
7.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
推荐引用方式
GB/T 7714		 Chen, Chao,Yu, Wenwen,Huang, Guangen,et al. Asymmetric macrocyclization enabled by Rh(III)-catalyzed C-H activation: Enantioenriched macrocyclic inhibitor of Zika virus infection[J]. CHINESE CHEMICAL LETTERS,2024,35(11):6.
APA Chen, Chao.,Yu, Wenwen.,Huang, Guangen.,Ren, Xuelian.,Chen, Xiangli.,...&Zhou, Bing.(2024).Asymmetric macrocyclization enabled by Rh(III)-catalyzed C-H activation: Enantioenriched macrocyclic inhibitor of Zika virus infection.CHINESE CHEMICAL LETTERS,35(11),6.
MLA Chen, Chao,et al."Asymmetric macrocyclization enabled by Rh(III)-catalyzed C-H activation: Enantioenriched macrocyclic inhibitor of Zika virus infection".CHINESE CHEMICAL LETTERS 35.11(2024):6.

入库方式： OAI收割

来源：上海药物研究所

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