The design and synthesis of nucleoside triphosphate isosteres as potential inhibitors of HIV reverse transcriptase

Richard Weaver, Ian H. Gilbert

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    Abstract

    We describe the synthesis of a variety of lipophilic isosteres of nucleoside triphosphates as potential anti-HIV agents. The citrate molecule proved to be a good mimic of triphosphate by modelling in terms of charge and spatial distribution. Several lipophilc derivatives of citrate were conjugated to the precedented anti-HIV nucleoside d4T via ester and amide linkages. A novel synthesis of 5'-amino-d4T is included. Intramolecular rearrangement of several amide-linked isosteres are also reported, along with an alternative synthetic strategy to the desired amide-linked isosteres. (C) 1997 Elsevier Science Ltd.

    Original languageEnglish
    Pages (from-to)5537-5562
    Number of pages26
    JournalTetrahedron
    Volume53
    Issue number15
    DOIs
    Publication statusPublished - 1997

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