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利用利贝斯金德-施罗格交叉偶联反应进行芳基方酰胺的固相合成。

Solid-phase synthesis of aryl squaramides using Liebeskind-Srogl cross-coupling.

作者信息

Chasák Jan, Brulíková Lucie

机构信息

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

出版信息

RSC Adv. 2025 May 2;15(18):14337-14353. doi: 10.1039/d5ra02225h. eCollection 2025 Apr 28.

DOI:10.1039/d5ra02225h
PMID:40322251
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12047450/
Abstract

We present a method for the synthesis of aryl-substituted squaramides through the Liebeskind-Srogl cross-coupling reaction performed on solid support. This approach offers a unique application for the cross-coupling reaction, allowing for the rapid and efficient production of a diverse range of substituted analogs within a combinatorial framework. Through our technique, we successfully synthesized derivatives that were previously unattainable. Additionally, the optimized conditions have been effectively applied in a scale-up reaction. The derivatives show potential for the treatment of drug-resistant tuberculosis.

摘要

我们展示了一种通过在固体载体上进行的利伯斯金德-施罗格交叉偶联反应来合成芳基取代方酰胺的方法。这种方法为交叉偶联反应提供了独特的应用，能够在组合框架内快速高效地生产多种取代类似物。通过我们的技术，我们成功合成了以前无法获得的衍生物。此外，优化后的条件已有效地应用于放大反应中。这些衍生物显示出治疗耐多药结核病的潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/40a11578d1d0/d5ra02225h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/afbca7e41362/d5ra02225h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/4f798b64a00d/d5ra02225h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/5af6f6d62d67/d5ra02225h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/fb1f799bded1/d5ra02225h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/49f885f8b0f5/d5ra02225h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/40a11578d1d0/d5ra02225h-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/afbca7e41362/d5ra02225h-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/4f798b64a00d/d5ra02225h-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/5af6f6d62d67/d5ra02225h-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/fb1f799bded1/d5ra02225h-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/49f885f8b0f5/d5ra02225h-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/ac17/12047450/40a11578d1d0/d5ra02225h-s5.jpg

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本文引用的文献

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The Liebeskind-Srogl Cross-Coupling Reaction as a Crucial Step in the Synthesis of New Squaramide-Based Antituberculosis Agents.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。
ACS Omega. 2024 Jul 29;9(32):34808-34828. doi: 10.1021/acsomega.4c04314. eCollection 2024 Aug 13.
2
Expanding the squaramide library as mycobacterial ATP synthase inhibitors: Innovative synthetic pathway and biological evaluation.扩展 squaramide 库作为分枝杆菌 ATP 合酶抑制剂：创新的合成途径和生物学评价。
Bioorg Med Chem. 2023 Nov 15;95:117504. doi: 10.1016/j.bmc.2023.117504. Epub 2023 Oct 18.
3
A tale of two inhibitors: diarylquinolines and squaramides.
双抑制剂的故事：二芳基喹啉类化合物和螺二酰胺类化合物。
EMBO J. 2023 Aug 1;42(15):e114912. doi: 10.15252/embj.2023114912. Epub 2023 Jul 12.
4
Mechanism of mycobacterial ATP synthase inhibition by squaramides and second generation diarylquinolines.分枝杆菌 ATP 合酶被 squaramides 和第二代二芳基喹啉类化合物抑制的机制。
EMBO J. 2023 Aug 1;42(15):e113687. doi: 10.15252/embj.2023113687. Epub 2023 Jun 28.
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Molecular docking-based interaction studies on imidazo[1,2-a] pyridine ethers and squaramides as anti-tubercular agents.基于分子对接的咪唑并[1,2-a]吡啶醚和瓜环酰胺类抗结核药物的相互作用研究。
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