53784-33-1Relevant articles and documents
Anomeric effect of the nitrogen atom in the isocyano and urea groups
Ichikawa, Yoshiyasu,Watanabe, Hitomi,Kotsuki, Hiyoshizo,Nakano, Keiji
, p. 6331 - 6337 (2010)
The anomeric effect associated with the nitrogen atom in the isocyano group was investigated by using 1H NMR spectroscopic analysis of an anomeric pair of xylopyranosyl isocyanides 8 and 7. We found that β-anomer 7 prefers to exist in the 1C4 conformation in which the nitrogen atom in the isocyano group adopts an axial orientation. This observation, coupled with the results of X-ray crystallographic analysis establishes that the nitrogen atom in the isocyano group displays the anomeric effect. Furthermore, xylopyranosyl isocyanides 8 and 7 were transformed into the corresponding xylopyranosyl ureas 10 and 11. In the case of the urea group, a normal sterically determined preference is observed in which the bulky urea substituents at the pyranose anomeric position occupy the equatorial position. Copyright
Synthesis of podophyllotoxin-glycosyl triazoles via click protocol mediated by silver (I)-N-heterocyclic carbenes and their anticancer evaluation as topoisomerase-II inhibitors
Nerella, Srinivas,Kankala, Shravankumar,Gavaji, Brahmeshwari
, p. 9 - 16 (2019/06/27)
Herein we report the regioselective synthesis of podophyllotoxin-Glycosyl triazole hybrids catalysed by Ag(I)-N-heterocyclic carbene (Ag(I)-NHC) in a short reaction time (～30 min) at ambient conditions. In principle, it is the first report of Click alkyne-azide cycloaddition catalysed by Ag(I)-NHC catalyst and moreover, this new methodology yielded good results when compared with traditional CuAAC in terms of reaction time and selectivity. The synthesised compounds were further explored for in vitro anticancer activity against four human cancer cell lines Du145, HeLa, A-549, and MCF-7 and found that these synthesised compounds possess significant anticancer activity. Further, the compounds 5a and 5e were identified as promising leads due to their better activity across all cell lines than that of the standard drug etoposide. Molecular docking studies of 5a & 5e with DNA Topoisomerase-II were revealed that the free energy calculations of active compounds were in good agreement with observed IC50 values.
Design, synthesis of oleanolic acid-saccharide conjugates using click chemistry methodology and study of their anti-influenza activity
Su, Yangqing,Meng, Lingkuan,Sun, Jiaqi,Li, Weijia,Shao, Liang,Chen, Kexuan,Zhou, Demin,Yang, Fan,Yu, Fei
, (2019/08/20)
The development of entry inhibitors is an emerging approach to the inhibition of influenza virus. In our previous research, oleanolic acid (OA) was discovered as a mild influenza hemagglutinin (HA) inhibitor. Herein, as a further study, we report the preparation of a series of OA-saccharide conjugates via the CuAAC reaction, and the anti-influenza activity of these compounds was evaluated in vitro. Among them, compound 11b, an OA-glucose conjugate, showed a significantly increased anti-influenza activity with an IC50 of 5.47 μM, and no obvious cytotoxic effect on MDCK cells was observed at 100 μM. Hemagglutination inhibition assay and docking experiment indicated that 11b might interfere with influenza virus infection by acting on HA protein. Broad-spectrum anti-influenza experiments showed 11b to be robustly potent against 5 different strains, including influenza A and B viruses, with IC50 values at the low-micromole level. Overall, this finding further extends the utility of OA-saccharide conjugates in anti-influenza virus drug design.
