2-O-glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones

Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F10%3A63509364" target="_blank" >RIV/70883521:28110/10:63509364 - isvavai.cz</a>
Result on the web
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DOI - Digital Object Identifier
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Result language
angličtina
Original language name
2-O-glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones
Original language description
Some saccharide derivatives of quinolin-2(1H)-one were isolated from natural sources. An example is zeanoside B, which was isolated from corn kernels. Various synthetic compounds of this class possess interesting biological activities; e.g., some 4-glycosyloxy-1-methylquinolin-2(1H)-ones have shown anti-allergic activity. Recently, we identified a method of the selective synthesis of 4-(?-D-glucopyranosyloxy)quinolin-2(1H)-ones by glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones. Herein wereport our actual study of glycosylation of N-unsubstituted 4-hydroxyquinolin-2(1H)-ones in other positions. Hydroxyl group of these compounds was protected by acetylation using acetic anhydride in pyridine and the 4-O-acetyl derivatives were treated with 2,3,4,6-tetra-O-acetyl-?-D-glucopyranosyl bromide and silver(I) oxide in acetonitrile. The reaction furnished 2-(2,3,4,6-tetra-O-acetyl-?-D-glucopyrano?syloxy)quinolin-4-yl acetates in satisfactory yields. Structures have been undoubted
Czech name
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Czech description
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Publication year
2010
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

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