C3′/C4′-Stereochemical Effects of Digitoxigenin α-L-/α-D-Glycoside in Cancer Cytotoxicity

Authors

  • John W. Hinds,

    1. Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
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  • Sean B. McKenna,

    1. Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
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  • Ehesan U. Sharif,

    1. Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
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  • Dr. Hua-Yu L. Wang,

    1. Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
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  • Dr. Novruz G. Akhmedov,

    Corresponding author
    1. Department of Chemistry, West Virginia University, 217 Clark Hall, Prospect Street, Morgantown, WV 26506 (USA)
    • Department of Chemistry, West Virginia University, 217 Clark Hall, Prospect Street, Morgantown, WV 26506 (USA)
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  • Prof. George A. O'Doherty

    Corresponding author
    1. Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
    • Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115 (USA)
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Abstract

original image

Sweet′n low in stereo: A Wharton reaction was employed along with a diastereoselective palladium-catalyzed glycosylation and other post-glycosylation transformations to synthesize digitoxin analogues. Cytotoxic evaluation against a panel of cancer cell lines uncovered the stereochemical and substitutional limits of the C3′/C4′-hydroxy functionality in digitoxin monosaccharide.

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