通过亚甲基或偶氮连接与炔单元相连的一些新型苯并呋喃-吡唑并[1,5-a]嘧啶杂化物的潜在 MRSA 抑制活性

IF 1.8 3区化学 Q3 CHEMISTRY, ORGANIC

Synthetic Communications Pub Date : 2024-09-28 DOI:10.1080/00397911.2024.2409875

Sherif M. H. Sanad , Ahmed E. M. Mekky

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引用次数: 0

摘要

MRSA 是一种导致严重感染的抗药性细菌，是研究人员开发新型抗药性化合物的目标。本研究旨在研究两个系列的苯并呋喃吡唑并[1,5-a]嘧啶 1 和 2 的 MRSA 抑制活性，这两个系列的苯并呋喃吡唑并[1,5-a]嘧啶分别通过亚甲基或偶氮连接到炔单元上。通过将苯并呋喃基烯丙酮 4 与适当的 1H-吡唑-3,5-二胺 5 在吡啶中回流反应 5-6 小时，制备出了所需的产品，产率为 82-92%。具有偶氮连接和带有电子释放基团的对位取代炔单元的产品表现出更高的抗菌活性。3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e 对金黄色葡萄球菌和大肠杆菌菌株的 MIC/MBC 值为 1.8/3.6 µM，其活性超过了参照物环丙沙星。此外，它对 MRSA ATCC:33591 和 ATCC:43300 菌株的 MIC/MBC 值分别为 3.6/14.4 µM 和 1.8/7.2 µM，显示出比参考药物利奈唑胺更有效的 MRSA 抑制活性。

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Potential MRSA inhibitory activity of some new benzofuran-pyrazolo[1,5-a]pyrimidine hybrids attached to arene units via methylene or azo linkage

MRSA, a resistant bacteria causing severe infections, is targeted by researchers developing new anti-resistance compounds. The study aimed to investigate the MRSA inhibitory activity of two series of benzofuran-pyrazolo[1,5-a]pyrimidines 1 and 2, attached to arene units via methylene or azo linkage, respectively. The desired products were prepared, in 82–92% yields, by reacting benzofuran-based enaminone 4 with the appropriate 1H-pyrazole-3,5-diamines 5 in pyridine at reflux for 5–6 h. The new hybrids showed a wide spectrum of antibacterial activity against different ATCC strains. Products with azo linkage and para-substituted arene units with electron-releasing groups demonstrated higher antibacterial activity. 3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e demonstrates activity that exceeded the reference ciprofloxacin with MIC/MBC values of 1.8/3.6 µM against S. aureus and E. coli strains. Also, it demonstrated more effective MRSA inhibitory activity than the reference linezolid, with MIC/MBC values of 3.6/14.4 and 1.8/7.2 µM against MRSA ATCC:33591 and ATCC:43300 strains, respectively.

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来源期刊

Synthetic Communications 化学-有机化学

CiteScore

4.40

自引率

4.80%

发文量

156

审稿时长

4.3 months

期刊介绍： Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.