50705-62-9Relevant academic research and scientific papers
Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity
Wang, Dong-dong,Li, Xiao-san,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Yao, Xin-sheng,Sun, Xue-Long,Tang, Jin-Shan
supporting information, p. 3359 - 3364 (2017/07/07)
Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.
Synthesis of l -Pyranosides by Hydroboration of Hex-5-enopyranosides Revisited
?opatkiewicz, Grzegorz,Mlynarski, Jacek
, p. 7545 - 7556 (2016/09/09)
Extensive study of the diastereoselective synthesis of l-pyranosides utilizing hydroboration of substituted exo-glucals (5-enopyranosides) obtained from d-sugars is presented. On the basis of this study we present the empirical rules describing the reacti
Aureolic Acid Group of Antibiotics: A Stereospecific Synthesis of Side Chain of Aglycone
Rao, A. V. Rama,Dhar, T. G. Murali,Gujar, M. K.,Yadav, J. S.
, p. 999 - 1000 (2007/10/02)
A stereospecific synthesis of the side chain (4) present in the aureolic acid group of antibiotics, starting from a D-glucose derivative (5) is described.
SYNTHESIS OF 2,3-ANHYDRO- AND 3,4-ANHYDRO-HEXOPYRANOSIDES HAVING A METHYL BRANCH ON THE OXIRANE RING, AND THEIR REACTIONS WITH SOME LITHIUM METHYLCUPRATE REAGENTS
Yoshimura, Juji,Kawauchi, Nobuya,Yasumori, Toshio,Sato, Ken-Ichi,Hashimoto, Hironobu
, p. 255 - 274 (2007/10/02)
Three 2,3-anhydroaldohexopyranosides having a 2-C-methyl or 3-C-methyl branch, as well as three 3,4-anhydroaldohexopyranosides having a 3-C-methyl (7) or 4-C-methyl branch, were newly synthesized.The reactions of these, together with those of a known 3-C-
