title: 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.
authors.affiliation: Department of Chemistry & Chemical Biology, Northeastern University, 117 Hurtig Hall, 360 Huntington Ave., Boston, MA 02115, USA.
authors.forename: John W
authors.initials: JW
authors.lastname: Hinds
authors.forename: Sean B
authors.initials: SB
authors.lastname: McKenna
authors.forename: Ehesan U
authors.initials: EU
authors.lastname: Sharif
authors.forename: Hua-Yu L
authors.initials: HY
authors.lastname: Wang
authors.forename: Novruz G
authors.initials: NG
authors.lastname: Akhmedov
authors.forename: George A
authors.initials: GA
authors.lastname: O'Doherty
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D002316:Cardiotonic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D045744:Cell Line, Tumor; D004073:Digitoxigenin / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004074:Digitoxin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D006031:Glycosylation; D006801:Humans; D009369:Neoplasms / Q000188:drug therapy; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000970:Antineoplastic Agents; D002316:Cardiotonic Agents; D004073:Digitoxigenin; D010165:Palladium; D004074:Digitoxin