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利贝斯金德-施罗格尔交叉偶联反应作为新型方酸酰胺类抗结核药物合成中的关键步骤。

The Liebeskind-Srogl Cross-Coupling Reaction as a Crucial Step in the Synthesis of New Squaramide-Based Antituberculosis Agents.

作者信息

Chasák Jan, Van Moll Laurence, Matheeussen An, De Vooght Linda, Cos Paul, Brulíková Lucie

机构信息

Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 77146 Olomouc, Czech Republic.

Laboratory of Microbiology, Parasitology and Hygiene (LMPH), S7, Faculty of Pharmaceutical, Biomedical and Veterinary Sciences, University of Antwerp, 2610 Wilrijk, Belgium.

出版信息

ACS Omega. 2024 Jul 29;9(32):34808-34828. doi: 10.1021/acsomega.4c04314. eCollection 2024 Aug 13.

DOI:10.1021/acsomega.4c04314
PMID:39157083
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11325506/
Abstract

The synthesis of an extensive series of new squaramides with high potential in treating drug-resistant tuberculosis employing the Liebeskind-Srogl cross-coupling reaction is presented. Using the protocol given and various substrates, we assessed the scope and limitations of our methodology and prepared an extensive range of desired compounds. Moreover, H NMR spectra in solution show the presence of two rotational conformers (rotamers) in special cases. The results of antimycobacterial activity demonstrate the highly selective substrate specificity of the tested squaramides, requiring an efficient and widely applicable synthetic approach needed for the discovery of lead compounds. Our synthetic strategy confirms the versatility of squaramides that can be easily transformed into diverse functionalized molecules.

摘要

本文介绍了利用利伯斯金德-施罗格交叉偶联反应合成一系列具有治疗耐药结核病高潜力的新型方酰胺。使用给定的方案和各种底物，我们评估了该方法的适用范围和局限性，并制备了大量所需化合物。此外，溶液中的氢核磁共振光谱表明，在特殊情况下存在两种旋转异构体（旋转异构体）。抗分枝杆菌活性结果表明，所测试的方酰胺具有高度选择性的底物特异性，这需要一种高效且广泛适用的合成方法来发现先导化合物。我们的合成策略证实了方酰胺的多功能性，它可以很容易地转化为各种功能化分子。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b122/11325506/be46204b80b5/ao4c04314_0008.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b122/11325506/81683acc98c4/ao4c04314_0010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b122/11325506/63396866b962/ao4c04314_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b122/11325506/582bcf107566/ao4c04314_0005.jpg
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