Citation: Chao Chen, Wenwen Yu, Guangen Huang, Xuelian Ren, Xiangli Chen, Yixin Li, Shenggui Liang, Mengmeng Xu, Mingyue Zheng, Yaxi Yang, He Huang, Wei Tang, Bing Zhou. Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection[J]. Chinese Chemical Letters, ;2024, 35(11): 109574. doi: 10.1016/j.cclet.2024.109574 shu

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

Chao Chen ^{a, b, c, g, 1} ,
Wenwen Yu ^{b, f, 1} ,
Guangen Huang ^{d, 1} ,
Xuelian Ren ^{e, 1} ,
Xiangli Chen ^d ,
Yixin Li ^{a, f} ,
Shenggui Liang ^{a, f} ,
Mengmeng Xu ^d ,
Mingyue Zheng ^{a, b} ,
Yaxi Yang ^{a, b, c, f, *,} ,
He Huang ^{a, e, *,} ,
Wei Tang ^{d, e, *,} ,
Bing Zhou ^{a, b, c, d, f, g, *,}

a.
School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China
b.
State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
c.
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China
d.
School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing 210023, China
e.
State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
f.
University of Chinese Academy of Sciences, Beijing 100049, China
g.
Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai 201203, China

Received Date: 10 December 2023
Revised Date: 24 January 2024
Accepted Date: 26 January 2024
Available Online: 2 February 2024

Figures(6)

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 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-H activation,
- Carboamidation,
- Enantioselective macrocyclization,
- Anti-Zika virus activity
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