银催化级联反应合成桥接等铬胺融合吡唑及其抗菌活性研究。

IF 8.7 Q1 CHEMISTRY, MULTIDISCIPLINARY
JACS Au Pub Date : 2025-08-26 eCollection Date: 2025-09-22 DOI:10.1021/jacsau.5c00105
Bhuvnesh Singh, Shreya Tewari, Manleen Kaur, Himanshu Sharma, Kumar Vanka, Neetu Singh, Ravi P Singh
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引用次数: 0

摘要

建立了一种立体选择性银催化的一锅乙烯醛加成反应,随后α-芳基吡唑啉酮与原位生成的等色胺离子发生级联[4+2]环加成反应,提供了前所未有的由等色胺、铬胺和吡唑单元组成的桥接[2.2.2][3.3.1]五环[5-6-6-6-6]骨架,作为一个单一的非对映体,产率很高。该方法具有反应条件温和、底物相容性好、可扩展性好、衍生化容易等特点。通过DFT研究阐明了反应机理。令人兴奋的是,在这里合成的前所未有的桥接等色体对革兰氏阳性和革兰氏阴性细菌表现出良好的选择性。我们证明,虽然一些结构是广谱抗菌,但有两种不同的结构可以探索选择性活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Bioinspired Synthesis of Bridged Isochromane Fused Pyrazoles by a Silver Catalyzed Cascade Reaction and Its Application for Antibacterial Activity.

A stereoselective silver catalyzed one pot vinylogous aldol addition followed by a cascade [4+2] cycloaddition reaction of α-arylidene pyrazolinones to in situ generated isochromenylium ions has been developed, which provides an unprecedented bridged [2.2.2] [3.3.1] pentacyclic [5-6-6-6-6] skeleton consisting of an isochroman, chroman, and a pyrazole unit in one molecule with good to high yields as a single diastereomer. This method offers mild reaction conditions, wide substrate compatibility, excellent scalability and easy derivatization. A DFT study was carried out to clarify the reaction mechanism. It was exciting to observe that the unprecedented bridged isochromans synthesized here have shown excellent selectivity toward Gram-positive and Gram-negative bacteria. We demonstrate that while some structures are broad spectrum antibacterial there are two distinct structures that can be explored for selective activity.

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CiteScore
9.10
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