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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.