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

IF 8.9 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Chinese Chemical Letters Pub Date : 2022-04-01 DOI:10.1016/j.cclet.2021.10.043

Tongyu Bi , Yi Xu , Xin Xu , Bixi Tang , Qing Yang , Yi Zang , Zhenyang Lin , Jia Li , Weibo Yang

引用次数: 2

Abstract

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-α, IL-6 and CCL2 mRNA expression.

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天然支架启发合成cf3取代大环内酯的催化碳氢烷基化大环化

开发创新的策略和方法来提供无法通过生物合成获得的天然类产品大环，但具有新颖的生物活性和简化的结构，是非常需要的。受雷帕霉素和FR252921的关键支架的启发，本文报道了Rh(III)催化的C-H烷基化大环化，从而可以获得cf3取代的大环内酯。DFT计算结果表明，碳-氢烷基化和烯烃大环化之间的化学选择性是高度可控的。此外，独特的cf3取代大环内酯类化合物对TNF-α、IL-6和CCL2 mRNA表达具有有效的抗炎活性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chinese Chemical Letters 化学-化学综合

CiteScore

14.10

自引率

15.40%

发文量

8969

审稿时长

1.6 months

期刊介绍： Chinese Chemical Letters (CCL) (ISSN 1001-8417) was founded in July 1990. The journal publishes preliminary accounts in the whole field of chemistry, including inorganic chemistry, organic chemistry, analytical chemistry, physical chemistry, polymer chemistry, applied chemistry, etc.Chinese Chemical Letters does not accept articles previously published or scheduled to be published. To verify originality, your article may be checked by the originality detection service CrossCheck.