Open AccessSynthesis and Evaluation of the α-d -/α-l -Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Antitumor Agents
Author(s) -
Hua Yu Leo Wang,
Yon Rojanasakul,
George A. O’Doherty
Publication year - 2011
Publication title -
acs medicinal chemistry letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.065
H-Index - 66
ISSN - 1948-5875
DOI - 10.1021/ml100290d
Subject(s) - digitoxigenin , chemistry , monosaccharide , cytotoxicity , tris , digitoxin , stereochemistry , glycosylation , dihydroxylation , stereoselectivity , apoptosis , biochemistry , glycoside , enantioselective synthesis , medicine , catalysis , in vitro , digoxin , heart failure
A highly regio- and stereo-selective asymmetric synthesis of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation followed by bis-/tris-dihydroxylation or bis-/tris-diimide reduction. The α-l-rhamnose and α-l-amicetose digitoxin monosaccharide analogues displayed stronger apoptosis inducing activity and cytotoxicity against non-small cell human lung cancer cells (NCI-H460) than its d-diastereomeric isomers in a sugar-chain length dependent manner.