5 ',5 '-Phosphodiesters and esterase labile triesters of 2 '-C-methylribonucleosides

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

    Research output: Contribution to journalArticleScientificpeer-review

    2 Citations (Scopus)

    Abstract

    Bis(2'-C-methyladenosin-5'-yl) (11), bis(2'-C-methylguanosin-5'-yl) (13), bis(2'-C-methyluridin-5'-yl) (15) and 2'-C-methylguanosin-5'-yl 2'-C-methyluridin-5'-yl (16) phosphodiesters have been prepared as pro-drug candidates for the respective 2'-C-methylribonucleoside 5'-monophosphates, expectedly exhibiting antiviral activity against Hepatitis C virus. Additionally, the bis(2'-C-methyladenosine) diester has been converted to 3-acetyloxymethoxy-2,2-bis(ethoxycarbonyl)propyl (19) or pivaloyloxymethyl (20) triester. The underlying idea is that the 5',5'-phosphodiester is first released by intracellular carboxyesterases and subsequently cleaved to nucleoside and nucleoside 5'-monophosphate by phosphodiesterases.

    Original languageEnglish
    Pages (from-to)226-243
    Number of pages18
    JournalARKIVOC
    Publication statusPublished - 2012
    Publication typeA1 Journal article-refereed

    Keywords

    • Pro-drug
    • antiviral
    • nucleotide
    • phosphoester
    • synthesis
    • CHRONIC HEPATITIS-C

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