Synthesis and Evaluation of the α-d-/α-l-Rhamnosyl and Amicetosyl Digitoxigenin Oligomers as Antitumor Agents | Zendy

Hua-Yu Leo Wang | Zendy; Yon Rojanasakul | Zendy; George A. O’Doherty | Zendy

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Synthesis 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.

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