铜催化和1,3-磺酰基迁移使氮杂吲哚在芳基环外围的安装：磺化吡咯[2,3-b]喹啉的合成和抗疟效力的研究

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-04-24 DOI:10.1021/acs.joc.5c00170

Shivani Choudhary, Gayyur, Siddhant, Ashan Manhas, Ruchir Kant, Nayan Ghosh

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引用次数: 0

摘要

本文采用一种廉价的铜催化剂，通过C-N， C-C和C-S键形成一系列磺化吡咯[2,3-b]喹啉，开发了一种原子高效的一锅方法。值得注意的是，反应是通过双环反应进行的，然后是1,3-磺酰基迁移序列。此外，该方法适用于广泛的2-羰基苯胺。此外，合成应用和放大反应突出了该协议的实用潜力。此外，磺化吡咯[2,3-b]喹啉类药物的抗疟特性在哺乳动物细胞中显示出对寄生虫的抑制作用，但没有细胞毒性作用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Copper-Catalyzed and 1,3-Sulfonyl Migration Enabled Installation of Azaindoles in the Periphery of Aryl Rings: Synthesis of Sulfonylated Pyrrolo[2,3-b]quinolines and Investigation of Antimalarial Potency

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Herein, an atom efficient and one-pot protocol, offering a series of sulfonylated pyrrolo[2,3-b]quinolines via C–N, C–C, and C–S bond formation, has been developed with an inexpensive copper catalyst. Notably, the reaction proceeds via a double-annulation reaction followed by a 1,3-sulfonyl migration sequence. Moreover, the method is applicable to a broad range of 2-carbonylanilines. Furthermore, synthetic applications and the scale-up reaction highlight the utility potential of this protocol. In addition, the antimalarial property of sulfonylated pyrrolo[2,3-b]quinolines showed parasite inhibition without cytotoxic effects in mammalian cells.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.