title: [Features phase transfer catalytic glycosylation of aromatic hydroxy acids].
abstract: The catalytic phase transfer reactions of per acetylated alpha-D-glucosaminyl chloride with isomeric hydroxybenzoic, 1-hydroxy-2-naphthoic acids in solid potassium carbonate--acetonitrile were studied. It was found that the composition and yields of reaction products are determined by the nature of the source ofcarboxylic acids, lipophilic phase transfer catalyst, temperature. For the first time found that the O-beta-glycosyl esters of ortho-hydroxyaromatic acids in the presence of potassium carbonate can anomerizovatsya in 1,2-cis derivatives. The structure of the synthesized compounds proved 1H NMR spectroscopy. In in vivo experiments it was established that glycosyl esters of salicylic acid and per acetylated 2-carboxy phenylglucosaminide exhibit analgesic activity similar to aspirin.
authors.forename: T A
authors.initials: TA
authors.lastname: Chupakhina
authors.forename: A A
authors.initials: AA
authors.lastname: Astrakhantseva
authors.forename: V O
authors.initials: VO
authors.lastname: Kur'ianov
mesh_terms: D000107:Acetylation; D000700:Analgesics / Q000008:administration & dosage* / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D002254:Carbonates / Q000737:chemistry; D002384:Catalysis; D004952:Esters / Q000008:administration & dosage / Q000737:chemistry*; D005944:Glucosamine / Q000031:analogs & derivatives / Q000737:chemistry*; D006031:Glycosylation; D006880:Hydroxy Acids / Q000008:administration & dosage / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009284:Naphthols / Q000737:chemistry; D010146:Pain / Q000188:drug therapy / Q000473:pathology; D044367:Phase Transition; D011188:Potassium / Q000737:chemistry; D051381:Rats; D020156:Salicylic Acid / Q000008:administration & dosage / Q000737:chemistry
chemical_list: D000700:Analgesics; D002254:Carbonates; D004952:Esters; D006880:Hydroxy Acids; D009284:Naphthols; C037593:potassium carbonate; D005944:Glucosamine; D020156:Salicylic Acid; D011188:Potassium; C050175:1-hydroxy-2-naphthoic acid