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Synthesis of some new cytidine and inosine derivatives
Faculty
Science
Year:
2005
Type of Publication:
Article
Pages:
2021-2026
Authors:
MOHAMED, EK, YOUSSIF, S, Ahmed, AFS, Ghoneim, AA
Journal:
BULLETIN OF THE KOREAN CHEMICAL SOCIETY KOREAN CHEMICAL SOC
Volume:
26
Research Area:
Chemistry
ISSN
ISI:000234694600024
Keywords :
inosine dialdehyde, 8-bromoinosine, 3-carbonylaminoinosines, 2 `, 4 `-dihydroxyhexopyranosyl hypoxanthine
Abstract:
The oxidation of cytidine 1 and inosine 5 by sodium metaperiodate followed by the reaction of the product with CH3I in NaOH afforded 2',4'-dihydroxyhexopyranosyl derivatives 2 and 14 respectively. The reaction of thiophene-2-carboxylic acid or furfural with cytidine were taken place via cycloaddition afforded adducts 3 and 4 respectivily. The bromination of inosine 5 or its 2',3'-O-isopropylidine inosine 6 led to the formation of 8-bromoanalogue 7 and 8, respectively. The reaction of 8-bromo-2',3'-O-isopropylidine inosine (8) with ethyl glycinate hydrochloride afforded 8-ethoxycarbonyiniethylaminoinosine 9. The alkylation of the compound 6 with urea led to the formation of 3-carbonylaminoinosine 10. The oxidation of 6 with DCC afforded 4'-formyl derivative 11, which on reaction with ethyl glycinate hydrochloride followed by reaction with sodium cyanoborohydride afforded 12, while the treatment of dialdehyde inosine 13 with ethyl cyanoacetate in the presence of 0.5 N NaOH afforded compound 15.
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