Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Some New Cytidine and Inosine Derivatives

  • Youssif, Shaker (Department of Chemistry, Faculty of Science, Zagazig University) ;
  • Mohamed, Enaiat K. (Department of Chemistry, Faculty of Science, Zagazig University) ;
  • Sayed Ahmed, Ahmed F. (Department of Chemistry, Faculty of Science, Zagazig University) ;
  • Ghoneim, Amira A. (Department of Chemistry, Faculty of Science, Zagazig University)
  • Published : 2005.12.20
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Abstract

The oxidation of cytidine 1 and inosine 5 by sodium metaperiodate followed by the reaction of the product with $CH_3I$ 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 ethylglycinate hydrochloride afforded 8-ethoxycarbonylmethylaminoinosine 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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  1. Synthesis of Some New Cytidine and Inosine Derivatives. vol.37, pp.16, 2005, https://doi.org/10.1002/chin.200616198