新型亚胺官能化1,3-重唑盐的合成、表征及应用

IF 5.4 3区 材料科学 Q2 CHEMISTRY, PHYSICAL
Attahir N.W. Kadafour, Halliru Ibrahim, Muhammad D. Bala
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引用次数: 1

摘要

n -取代1,3-重唑与2-溴乙基氨基甲基萘酚进行简单无溶剂季铵化反应,得到3种新的席夫碱(SB或亚胺)功能化1,3-重唑[3 (SB-咪唑),4和5 (SB-苯并咪唑)]盐。对化合物进行了光谱表征,并用x射线衍射分析了化合物3[3-(2-(2-羟基萘-1-基)亚甲基)氨基)乙基)甲基咪唑-3-六氟磷酸铵]的单晶固体结构。作为抗菌药物进行试验时,每种盐对革兰氏阳性金黄色葡萄球菌ATCC 25923菌株和耐甲氧西林金黄色葡萄球菌ATCC 700699 (MRSA)菌株均有显著活性,记录的最佳最小抑制浓度(MIC)值为1.25µg/mL。虽然活性不如阳性对照环丙沙星,但观察到的化合物活性与报道的一些标准抗生素相当,并且明显优于文献中报道的类似的1,3-重唑盐。理论分子对接的使用支持了盐的实验MIC值。这是因为3、4和5的估计负结合能分别为-6.45、-7.27和-7.84千卡/摩尔,表明与MRSA脂肪酶复合物结合良好。此外,溶血试验的结果证实了抗菌试验的结果,即在盐的最活跃浓度(最低MIC值)下,红细胞溶血率≤5%。综上所述,抗菌活性研究结果和在安全溶血百分比范围内的负吉布斯结合能使新唑盐成为药物设计的良好模板。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Synthesis, characterization and application of new imino-functionalized 1,3-diazolium salts as antimicrobial agents

The simple solventless quaternization of N-substituted 1,3-diazoles with 2-bromoethyliminomethylnaphthol yielded three new Schiff base (SB or imine)-functionalized 1,3-diazolium [3 (SB-imidazolium), 4 and 5 (SB-benzimidazolium)] salts. The compounds were characterized spectroscopically, and the single-crystal solid-state structure of compound 3 [3-(2-(2-hydroxynaphthalen-1-yl) methylene) amino) ethyl) methylimidazol-3-ium hexafluorophosphate] was analyzed by X-ray diffraction. When tested as antimicrobials, each salt gave significant activity against the Gram-positive Staphylococcus aureus ATCC 25923 strain and the Methicinin resistant Staphylococcus aureus ATCC 700699 (MRSA) strain with the best minimum inhibitory concentration (MIC) value of 1.25 µg/mL recorded for 4. Although not as active as the positive control, Ciprofloxacin, the observed activities of the compounds are comparable to those reported for some standard antibiotics and significantly better than similar 1,3-diazolium salts that are already reported in the literature. The use of theoretical molecular docking supports the experimental MIC values for the salts. This is because the estimated negative binding energies of -6.45, -7.27 and -7.84, kcal/mol for 3, 4 and 5, respectively, indicated favourable binding with the MRSA lipase enzyme complexes. Furthermore, the results of a hemolytic assay corroborated the antimicrobial test results, which showed ≤5% hemolysis of red blood cells at the most active concentration (lowest MIC value) recorded for the salts. In summary, the results of the antibacterial activity study and the negative Gibbs binding energies that are within safe hemolysis percentages make the new azolium salts good templates in drug design.

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来源期刊
ACS Applied Energy Materials
ACS Applied Energy Materials Materials Science-Materials Chemistry
CiteScore
10.30
自引率
6.20%
发文量
1368
期刊介绍: ACS Applied Energy Materials is an interdisciplinary journal publishing original research covering all aspects of materials, engineering, chemistry, physics and biology relevant to energy conversion and storage. The journal is devoted to reports of new and original experimental and theoretical research of an applied nature that integrate knowledge in the areas of materials, engineering, physics, bioscience, and chemistry into important energy applications.
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