Rhodium(III)-Catalyzed C-H/O2 Dual Activation and Macrocyclization: Synthesis and Evaluation of Pyrido[2,1-a]isoindole Grafted Macrocyclic Inhibitors for Influenza H1N1
文献类型：期刊论文
| 作者 | Song, Bichao4,5; Guo, Xueying3; Yang, Li4,5; Yu, Haiyue4,5; Zong, Xinlei2; Liu, Xiujuan1,4; Wang, Hao4,5; Xu, Zhongliang4,5; Lin, Zhenyang3; Yang, Weibo1,2,4,5
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| 刊名 | ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
 |
| 出版日期 | 2023-04-03 |
| 卷号 | 62期号:15 |
| 关键词 | C-H Activation Macrocyclization Multicomponent Coupling O-2 Activation Rh Catalysis |
| DOI | 10.1002/anie.202218886 |
| 文献子类 | Article |
| 英文摘要 | The development of environment-friendly, step economic couplings to generate structurally diverse macrocyclic compounds is highly desirable but poses a marked challenge. Inspired by the C-H oxidation mechanism of cytochromes P450, an unprecedented and practical Rh-III-catalyzed acylmethylation macrocyclization via C-H/O-2 dual activation has been developed by us. The process of macrocyclization is facilitated by a synergic coordination from pyridine and ester group. Interestingly, the reaction mode derives from a three-component coupling which differs from established olefination and alkylation paths. Density functional theory (DFT) calculations and control experiments revealed the mechanism of this unique C-H/O-2 dual activation. The newly achieved acylmethylation macrocyclic products and their derivatives showed a potent anti-H1N1 bioactivity, which may provide an opportunity for the discovery of novel anti-H1N1 macrocyclic leading compounds. |
| WOS关键词 | C-H ACTIVATION ; HYDROXYLATION ; ANTIFUNGAL ; PEPTIDES ; TRYPTOPHAN ; DISCOVERY ; KETONES |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000942269000001 |
| 出版者 | WILEY-V C H VERLAG GMBH |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/309683]  |
| 专题 | 新药研究国家重点实验室 |
| 通讯作者 | Lin, Zhenyang; Yang, Weibo |
| 作者单位 | 1.Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Pharmaceut Sci & Technol, Hangzhou 310024, Peoples R China 2.Nanjing Univ Chinese Med, Sch Chinese Mat Med, Nanjing 210000, Peoples R China; 3.Hong Kong Univ Sci & Technol, Dept Chem, Clear Water Bay, Hong Kong, Peoples R China; 4.Univ Chinese Acad Sci, Beijing 100049, Peoples R China; 5.Chinese Acad Sci, Shanghai Inst Mat Med, State key Lab Drug Res, Shanghai 201203, Peoples R China; |
| 推荐引用方式 GB/T 7714 | Song, Bichao,Guo, Xueying,Yang, Li,et al. Rhodium(III)-Catalyzed C-H/O2 Dual Activation and Macrocyclization: Synthesis and Evaluation of Pyrido[2,1-a]isoindole Grafted Macrocyclic Inhibitors for Influenza H1N1[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,2023,62(15). |
| APA | Song, Bichao.,Guo, Xueying.,Yang, Li.,Yu, Haiyue.,Zong, Xinlei.,...&Yang, Weibo.(2023).Rhodium(III)-Catalyzed C-H/O2 Dual Activation and Macrocyclization: Synthesis and Evaluation of Pyrido[2,1-a]isoindole Grafted Macrocyclic Inhibitors for Influenza H1N1.ANGEWANDTE CHEMIE-INTERNATIONAL EDITION,62(15). |
| MLA | Song, Bichao,et al."Rhodium(III)-Catalyzed C-H/O2 Dual Activation and Macrocyclization: Synthesis and Evaluation of Pyrido[2,1-a]isoindole Grafted Macrocyclic Inhibitors for Influenza H1N1".ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 62.15(2023). |
入库方式： OAI收割
来源：上海药物研究所
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