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Iridium-Catalyzed Direct and Site-Selective C-H Heteroarylation, Alkenylation, and Alkylation of Indoles

文献类型：期刊论文

作者Cao, Tian4,5; Hu, Wanqi3,5; Hao, Linlu3,5; Guo, Liting3,5; Wu, Li5; Xu, Lei5; Gao, Zhaobing3,5,7; Li, Jia1,2,3,5,6; Tian, Fuyun5; Wu, Xiaowei3,5,7
刊名JOURNAL OF ORGANIC CHEMISTRY
出版日期2025-12-05
卷号90期号:48页码:17128-17139
ISSN号0022-3263
DOI10.1021/acs.joc.5c02429
通讯作者Li, Jia(jli@simm.ac.cn) ; Tian, Fuyun(tianfuyun@zidd.ac.cn) ; Wu, Xiaowei(wuxiaowei@simm.ac.cn)
英文摘要Indoles and coumarins represent prominent structural motifs in a wide range of biologically active molecules. Combining these two privileged scaffolds offers immense potential for innovation in drug discovery. Herein, we unveil a regioselective iridium-catalyzed approach for the direct C-H heteroarylation, alkenylation, and alkylation of indoles using iodonium ylides through a metal carbene-induced C-H insertion mechanism, accessing a series of novel 4-hydroxy-3-indolyl-coumarins and analogues. The method demonstrates a wide substrate scope, good tolerance for functional groups, scalability with low catalyst loading (as low as 0.2 mol %), and mild reaction conditions. Notably, Compound 3v significantly enhanced GABAARs-alpha 1 beta 3 gamma 2L activity, suggesting potential as a lead for antiepileptic and sedative drug discovery. Moreover, preliminary screening assays indicate that some other compounds exhibit moderate inhibitory effects against the pancreatic cancer cell line.
WOS关键词DIARYLIODONIUM SALTS ; DIRECT ALKYNYLATION ; ARYLATION ; FUNCTIONALIZATION ; PYRROLES ; CASCADE ; ALKYNES ; RH(III)
资助项目Shanghai Institute of Materia Medica, Chinese Academy of Sciences[SIMM0420245007] ; Basic and Applied Basic Research Foundation of Guangdong Province[E404005] ; Natural Science Foundation of Zhongshan Municipality[221018194369472] ; National Natural Science Foundation of China[82404416] ; Shandong Laboratory Program[SYS202205] ; High-level Innovative Research Institute[2021B0909050003] ; Zhongshan Science and Technology Bureau[CXTD2022013]
WOS研究方向Chemistry
语种英语
WOS记录号WOS:001620827000001
出版者AMER CHEMICAL SOC
源URL[http://119.78.100.183/handle/2S10ELR8/322025]  
专题中国科学院上海药物研究所
通讯作者Li, Jia; Tian, Fuyun; Wu, Xiaowei
作者单位1.Bohai Rim Adv Res Inst Drug Discovery, Shandong Lab Yantai Drug Discovery, Yantai 264117, Shandong, Peoples R China
2.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Chem Biol, Shanghai 201203, Peoples R China
3.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210023, Peoples R China
4.Guizhou Med Univ, Sch Pharmaceut Sci, State Key Lab Discovery & Utilizat Funct Component, Guiyang 550014, Peoples R China
5.Chinese Acad Sci, Zhongshan Inst Drug Discovery, Shanghai Inst Mat Med, Zhongshan 528400, Peoples R China
6.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China
7.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China
推荐引用方式
GB/T 7714		 Cao, Tian,Hu, Wanqi,Hao, Linlu,et al. Iridium-Catalyzed Direct and Site-Selective C-H Heteroarylation, Alkenylation, and Alkylation of Indoles[J]. JOURNAL OF ORGANIC CHEMISTRY,2025,90(48):17128-17139.
APA Cao, Tian.,Hu, Wanqi.,Hao, Linlu.,Guo, Liting.,Wu, Li.,...&Wu, Xiaowei.(2025).Iridium-Catalyzed Direct and Site-Selective C-H Heteroarylation, Alkenylation, and Alkylation of Indoles.JOURNAL OF ORGANIC CHEMISTRY,90(48),17128-17139.
MLA Cao, Tian,et al."Iridium-Catalyzed Direct and Site-Selective C-H Heteroarylation, Alkenylation, and Alkylation of Indoles".JOURNAL OF ORGANIC CHEMISTRY 90.48(2025):17128-17139.

入库方式： OAI收割

来源：上海药物研究所

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