C5′-alkyl substitution effects on digitoxigenin α-l-glycoside cancer cytotoxicity
A highly regio- and stereoselective asymmetric synthesis of various C5′-alkyl side chains of rhamnosyl- and amicetosyl-digitoxigenin analogues has been established via palladium-catalyzed glycosylation with postglycosylated dihydroxylation or diimide reduction. The C5′-methyl group in both α-l-rhamnose and α-l-amicetose digitoxin analogues displayed a steric directed apoptosis induction and tumor growth inhibition against nonsmall cell human lung cancer cells (NCI-H460). The antitumor activity is significantly reduced when the steric hindrance is increased at the C5′-stereocenter.
Wang, Hua-Yu Leo,Wu, Bulan,Zhang, Qi,Kang, Sang-Woo,Rojanasakul, Yon,O'Doherty, George A.
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p. 259 - 263
(2011/06/16)
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