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  • Title: Synthesis and in vitro anti-hepatitis B virus activity of six-membered azanucleoside analogues.
    Author: Wang D, Li YH, Wang YP, Gao RM, Zhang LH, Ye XS.
    Journal: Bioorg Med Chem; 2011 Jan 01; 19(1):41-51. PubMed ID: 21183354.
    Abstract:
    Fifteen novel six-membered azanucleoside derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. The most potent compound 16b with an IC(50) value of 2.74μg/mL (lower than 3TC) and a SI value of 13.5 was disclosed. The key synthetic steps involved the rearrangement of lactones (which were readily obtained from monosaccharides) and the Lewis acid-catalyzed condensation of nucleobases with azasugar donors. Using the versatile acetylated azasugar donors, azanucleosides covering three types of azasugars and four types of natural nucleobases were successfully obtained. The experimental results showed that some six-membered azanucleosides may find applications in the discovery of new anti-viral agents.
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