934021-75-7Relevant academic research and scientific papers
A direct comparison of the anticancer activities of digitoxin MeON-Neoglycosides and O-Glycosides
Iyer, Anand Krishnan V.,Zhou, Maoquan,Azad, Neelam,Elbaz, Hosam,Wang, Leo,Rogalsky, Derek K.,Rojanasakul, Yon,O'Doherty, George A.,Langenhan, Joseph M.
scheme or table, p. 326 - 330 (2010/12/18)
Digitoxin is a cardiac glycoside currently being investigated for potential use in oncology; however, an investigation of anticancer activity as a function of oligosaccharide chain length has not yet been performed. We generated mono-, di-, and tri-O-digitoxoside derivatives of digitoxin and compared their activities to the corresponding MeON-neoglycosides. Both classes of cardenolide derivatives display comparable oligosaccharide chain length-dependent cytotoxicity toward human cancer cell lines. Further investigation revealed that both classes of compounds induce caspase-9-mediated apoptosis in non-small cell lung cancer cells (NCI-H460). Because O-glycosides and MeON-neoglycosides share a similar mode of action, the convenience of MeON-neoglycosylation could be exploited in future SAR work to rapidly survey large numbers of carbohydrates to prioritize selected O-glycoside candidates for traditional synthesis.
De novo synthesis of the trisaccharide subunit of landomycins A and E
Zhou, Maoquan,O'Doherty, George A.
scheme or table, p. 2283 - 2286 (2009/05/11)
(Chemical Equation Presented) A highly enantio- and diastereoselective synthesis of α-L-rhodinose, β-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium
De novo approach to 2-deoxy-β-glycosides: Asymmetric syntheses of digoxose and digitoxin
Zhou, Maoquan,O'Doherty, George A.
, p. 2485 - 2493 (2008/02/02)
A highly enantioselective and straightforward route to trisaccharide natural products digoxose and digitoxin has been developed. Key to this approach is the iterative application of the palladium-catalyzed glycosylation reaction, reductive 1,3-transposition, diastereoselective dihydroxylation, and regioselective protection. The first total synthesis of natural product digoxose was accomplished in 19 total steps from achiral 2-acylfuran, and digitoxin was fashioned in 15 steps starting from digitoxigenin 2 and pyranone 8β. This flexible synthetic strategy also allows for the preparation of mono- and disaccharide analogues of digoxose and digitoxin.
