C3′/C4′‐Stereochemical Effects of Digitoxigenin α‐ L ‐/α‐ D ‐Glycoside in Cancer Cytotoxicity | Zendy

Hinds John W. | Zendy; McKenna Sean B. | Zendy; Sharif Ehesan U. | Zendy; Wang HuaYu L. | Zendy; Akhmedov Novruz G. | Zendy; O'Doherty George A. | Zendy

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

Author(s) -

Hinds John W.,

McKenna Sean B.,

Sharif Ehesan U.,

Wang HuaYu L.,

Akhmedov Novruz G.,

O'Doherty George A.

Publication year - 2013

Publication title -

chemmedchem

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.817

H-Index - 100

eISSN - 1860-7187

pISSN - 1860-7179

DOI - 10.1002/cmdc.201200465

Subject(s) - digitoxigenin , digitoxin , glycosylation , chemistry , monosaccharide , stereochemistry , glycoside , cytotoxicity , cancer cell lines , cancer cell , biochemistry , cancer , biology , digoxin , heart failure , medicine , genetics , in vitro

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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