title: [Glycosides of hydroxylamine derivatives. I. phase transfer synthesis and study of isatine-3-oximes glucosaminides influence on bacterial luminescence].
abstract: In the phase transfer system solid calcium carbonate-acetonitrile, per acetate alpha-D-glucosaminilchloride glycosilate easily deprotoned isatine-3-oximes hydroxyl groups. It was found that the presence in the reaction mixture a catalytic amounts of 15-crown-5 accelerated the process twice. Obtained O-beta-D-glucosaminides were identified with 1H-NMR spectroscopy. Features of synthesized compound's NMR spectra are discussed in comparison with those of another N-acetylglucosamine 1-O-derivatives. The biological activity of the some oximes with different substituents in isatin residuum has been studied in a test of inhibition of bioluminescence of marine luminescent bacteria Photobacterium leiognathi Sh12. The nature of N-substituent of isatin fragment and 5-substituent of isatin main structure is compared with glycosides ability to suppress bacterial luminescence.
authors: V O
authors: VO
authors: Kur'ianov
authors: T A
authors: TA
authors: Chupakhina
authors: A A
authors: AA
authors: Shapovalova
authors: A M
authors: AM
authors: Katsev
authors: V Ia
authors: VIa
authors: Chirva
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D002119:Calcium Carbonate / Q000737:chemistry; D002384:Catalysis; D043844:Crown Ethers / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis* / Q000378:metabolism / Q000494:pharmacology; D019811:Hydroxylamine / Q000138:chemical synthesis* / Q000378:metabolism; D007510:Isatin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D049449:Luminescence; D008163:Luminescent Measurements; D009682:Magnetic Resonance Spectroscopy; D044367:Phase Transition / Q000187:drug effects; D010776:Photobacterium / Q000187:drug effects / Q000502:physiology*
chemical_list: D000097:Acetonitriles; D000900:Anti-Bacterial Agents; D043844:Crown Ethers; D005960:Glucosides; C445199:isatin-3-oxime-glucoside; D019811:Hydroxylamine; C042148:15-crown-5; D007510:Isatin; D002119:Calcium Carbonate; C032159:acetonitrile