Synthesis of the fully acetylated 8-hydroxyquinoline O-β-D-glucosaminides and its 2-methyl- and 5-chloro-derivatives was conducted in the phase transfer catalytic system of solid potassium carbonateanhydrous acetonitrile. The respective triols were obtained by deacetylation according to Zemplen. The structure of all synthesized compounds was proven by 1H NMR spectroscopy. Antimicrobial activity of the non-protected glycosides was investigated using the luminescence inhibition test with marine luminous bacteria Vibrio fischeri F1 as well as by the serial dilution method with Escherichia coli, Agrobacterium tumefaciens, Bacillus cereus, and Micrococcus luteus strains from culture collection. It was found that the coupling of N-acetyl-β-D-glucosamidine residue decreased antimicrobial activity in comparison with non-glycosylated forms of quinoline.

中文翻译：

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8-羟基喹啉氨基葡萄糖的合成及抗菌活性研究

在固体碳酸钾无水乙腈的相转移催化体系中合成了完全乙酰化的 8-羟基喹啉 O-β-D-氨基葡萄糖及其 2-甲基和 5-氯衍生物。根据Zemplen通过脱乙酰作用获得相应的三醇。所有合成化合物的结构均通过 1H NMR 光谱证实。使用海洋发光细菌 Vibrio fischeri F1 的发光抑制试验以及使用来自培养物保藏中心的大肠杆菌、根癌农杆菌、蜡状芽孢杆菌和藤黄微球菌菌株的连续稀释方法研究了未受保护的糖苷的抗菌活性。发现与非糖基化形式的喹啉相比，N-乙酰基-β-D-葡糖脒残基的偶联降低了抗菌活性。