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

Abstract
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.
AuthorsJohn W Hinds, Sean B McKenna, Ehesan U Sharif, Hua-Yu L Wang, Novruz G Akhmedov, George A O'Doherty
JournalChemMedChem (ChemMedChem) Vol. 8 Issue 1 Pg. 63-9 (Jan 2013) ISSN: 1860-7187 [Electronic] Germany
PMID23139074 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Chemical References
  • Antineoplastic Agents
  • Cardiotonic Agents
  • Digitoxigenin
  • Palladium
  • Digitoxin
Topics
  • Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
  • Cardiotonic Agents (chemical synthesis, chemistry, pharmacology)
  • Catalysis
  • Cell Line, Tumor
  • Digitoxigenin (chemical synthesis, chemistry, pharmacology)
  • Digitoxin (analogs & derivatives, chemical synthesis, pharmacology)
  • Drug Screening Assays, Antitumor
  • Glycosylation
  • Humans
  • Neoplasms (drug therapy)
  • Palladium (chemistry)
  • Stereoisomerism

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