与芳烃单元连接的新型双(噻吩[2,3-b]吡啶)杂合体作为潜在的细菌生物膜和MRSA抑制剂

IF 1.1 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY
S. Sanad, Ahmed E. M. Mekky
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引用次数: 2

摘要

本研究以哌嗪为媒介,利用超声技术制备了新的芳烃连接双(噻吩[2,3-b]吡啶)杂合体。在1.4等量哌嗪的存在下,双α-卤代酮与2等量吡啶-2(1H)-硫酮反应制备了目标杂合体。将反应混合物在60℃下超声处理30-40 min,产率为88-95%。当对六种不同的ATCC菌株进行测试时,新产品显示出广泛的抗菌活性。4-(4-甲氧基苯基)连锁杂种1i和1j分别与6-(4-甲氧基苯基)和6-(对tolyl)单位结合,对金黄色葡萄球菌、粪肠球菌、大肠杆菌和铜绿假单胞菌的杀伤效果最好。两种杂交种的MIC和MBC分别在2.0 ~ 2.1 μM和4.1 ~ 4.2 μM之间,均优于对照环丙沙星。此外,杂种1i和1j对MRSA ATCC:33591和ATCC:43300的MIC值为2.0 ~ 4.2µM, MBC值为8.2 ~ 8.5µM,均优于利奈唑胺。此外,杂种1i和1j表现出与标准环丙沙星相当的抑菌生物膜活性。对金黄色葡萄球菌、粪孢杆菌、大肠杆菌和铜绿假单胞菌的IC50值为3.8 ~ 4.6 μM。杂合物1i和1j对人乳腺上皮细胞系MCF-10A的细胞毒性证明了这两种杂合物作为安全抗菌剂的潜力。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
New bis(thieno[2,3-b]pyridine) hybrids linked to arene units as potential bacterial biofilm and MRSA inhibitors
Using sonication and mediated by piperazine, new arene-linked bis(thieno[2,3-b]pyridine) hybrids were efficiently prepared in this study. The target hybrids were prepared by reacting bis(α-haloketone) with two equivalents of the appropriate pyridine-2(1H)-thiones in the presence of 1.4 equivalents of piperazine. The reaction mixture was subjected to sonication at 60 °C for 30-40 min to produce the desired products in 88-95% yields. When tested against six different ATCC bacterial strains, the new products demonstrated a wide range of antibacterial activity. The 4-(4-methoxyphenyl)-linked hybrids 1i, and 1j, attached to 6-(4-methoxyphenyl) and 6-(p-tolyl) units, respectively, had the best efficacy against S. aureus, E. faecalis, E. coli, and P. aeruginosa strains. Both hybrids showed more effective potency than the reference ciprofloxacin with MIC and MBC values in the ranges from 2.0-2.1, and 4.1-4.2 μM, respectively. Additionally, hybrids 1i, and 1j demonstrated stronger efficacy than linezolid with MIC values ranging from 2.0-4.2 µM, and MBC values ranging from 8.2-8.5 µM, respectively, against the MRSA ATCC:33591, and ATCC:43300 strains. Furthermore, hybrids 1i, and 1j showed inhibitory antibacterial biofilm activity comparable to the standard ciprofloxacin. They had IC50 values ranging from 3.8-4.6 μM against S. aureus, E. faecalis, E. coli, and P. aeruginosa strains. The cytotoxicity of hybrids 1i, and 1j against the human breast epithelial cell line MCF-10A lends credence to both hybrids' potential as safe antibacterial agents.
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来源期刊
Canadian Journal of Chemistry
Canadian Journal of Chemistry 化学-化学综合
CiteScore
1.90
自引率
9.10%
发文量
99
审稿时长
1 months
期刊介绍: Published since 1929, the Canadian Journal of Chemistry reports current research findings in all branches of chemistry. It includes the traditional areas of analytical, inorganic, organic, and physical-theoretical chemistry and newer interdisciplinary areas such as materials science, spectroscopy, chemical physics, and biological, medicinal and environmental chemistry. Articles describing original research are welcomed.
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