Synthesis and investigation of antimicrobial activity of 8-hydroxyquinoline glucosaminides

Synthesis of the fully acetylated 8-hydroxyquinoline O-beta-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 H-1 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-beta-D-glucosamidine residue decreased antimicrobial activity in comparison with non-glycosylated forms of quinoline.