Synthesis of 3',5'-Cyclic Phosphate and Thiophosphate Esters of 2'-C-Methyl Ribonucleosides

Anna Leisvuori, Zafar Ahmed, Mikko Ora, Leonid Beigelman, Lawrence Blatt, Harri Lonnberg

    Research output: Contribution to journalArticleScientificpeer-review

    10 Citations (Scopus)

    Abstract

    2'-C-Methylnucleosides are known to exhibit antiviral activity against Hepatitis C virus. Since the inhibitory activity depends on their intracellular conversion to 5'-triphosphates, dosing as appropriately protected 5'-phosphates or 5'-phosphorothioates appears attractive. For this purpose, four potential pro-drugs of 2'-C-methylguanosine, i.e., 3',5'-cyclic phosphorothioate of 2'-C-methylguanosine and 2'-C,O6-dimethylguanosine, 1 and 2, respectively, the S-[(pivaloyloxy)methyl] ester of 2'-C,O6-dimethylguanosine 3',5'-cyclic phosphorothioate and the O-methyl ester of 2'-C,O6-dimethylguanosine 3',5'-cyclic phosphate, 3 and 4, respectively, have been prepared.

    Original languageEnglish
    Pages (from-to)1512-1520
    Number of pages9
    JournalHELVETICA CHIMICA ACTA
    Volume95
    Issue number9
    DOIs
    Publication statusPublished - Sep 2012
    Publication typeA1 Journal article-refereed

    Keywords

    • Nucleosides
    • Prodrugs
    • Phosphorothioate
    • HEPATITIS-C-VIRUS
    • MONOPHOSPHATE PRODRUGS

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