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Design, synthesis and antimicrobial evaluation of thioglycosides of a novel class of 2-mercaptonicotinonitriles
Journal of Saudi Chemical Society ( IF 5.6 ) Pub Date : 2020-11-10 , DOI: 10.1016/j.jscs.2020.11.001
Amira Atef Ghoneim , Wael Abdelgayed Ahmed Arafa

A new class of thioglycosides comprising a diazenyl pyridine moiety was assembled from the regioselective reaction of the acetylated α-glycopyranosyl bromide with hitherto unreported 2-mercaptonicotinonitriles. Moreover, the deacetylation of S-glycoside derivatives utilizing of methanolic ammonia solution afforded the free hydroxy thioglycosides in quantitative yields. The identity of the newly obtained derivatives has been achieved via spectroscopic and elemental analyses. All of the newly synthesized derivatives exhibited significant antimicrobial activity towards certain selected microorganisms (bacteria and fungi). Generally, S-glycoside derivatives demonstrated outstanding antibacterial and antifungal activities. Amongst them, the acetylated derivatives showed the most distinguished antifungal and antibacterial activities with a promising minimum inhibitory concentration (MIC) values in comparison with the approved drugs; Amphotericin B and Cefotaxime.



中文翻译:

一类新型2-巯基巯基腈的硫代糖苷的设计,合成和抗菌性评估

从乙酰化的α-甘露糖基溴化物与迄今未报道的2-巯基二十碳四烯腈的区域选择性反应中组装了一种新的包含二氮烯基吡啶部分的硫代糖苷。此外,利用甲醇氨溶液使S-糖苷衍生物脱乙酰基以定量收率得到游离的羟基硫代糖苷。新获得的衍生物的身份已通过光谱和元素分析获得。所有新合成的衍生物均对某些选定的微生物(细菌和真菌)表现出显着的抗菌活性。通常,S-糖苷衍生物表现出杰出的抗菌和抗真菌活性。其中,与已批准的药物相比,乙酰化衍生物显示出最杰出的抗真菌和抗菌活性,并有希望的最小抑菌浓度(MIC)值。两性霉素B和头孢噻肟。

更新日期:2020-11-12
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