70223-97-1Relevant articles and documents
Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents
Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan
, (2021/12/30)
In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.
Synthesis and antimicrobial studies of novel n-glycosyl hydrazino carbothioamide
Nayak, Riddhi A.,Mangte, Anvita D.
, p. 127 - 131 (2021/01/06)
In view of applications of N-glycosylated compounds in medicinal chemistry and in many other ways, herein the synthesis of novel N-glycosyl hydrazino carbothioamides is reported. New N-glycosyl hydrazino carbothioamides were synthesized by the condensation of per-O-acetyl glycosyl isothiocyanate with different aromatic hydrazides. The newly synthesized compounds were characterized by using the IR, 1H NMR and mass spectral studies. Antimicrobial evaluation of the synthesized N-glycosyl hydrazino carbothioamide was also examined. Antimicrobial activities of the synthesized compound were evaluated against bacteria E. coli, P. aeruginosa, S. aureus, S. pyogenus and fungi C. albicans, A. niger and A. clavatus. All the N-glycosyl hydrazino carbothioamides exhibit promising antimicrobial activity.
Controlling the Kinetics of Self-Reproducing Micelles by Catalyst Compartmentalization in a Biphasic System
Post, Elias A. J.,Fletcher, Stephen P.
, p. 2741 - 2755 (2019/02/26)
Compartmentalization of reactions is ubiquitous in biochemistry. Self-reproducing lipids are widely studied as chemical models of compartmentalized biological systems. Here, we explore the effect of catalyst location on copper-catalyzed azide-alkyne cycloadditions which drive the self-reproduction of micelles from phase-separated components. Tuning the hydrophilicity of the copper-ligand complex, so that hydro-phobic or -philic catalysts are used in combination with hydro-philic and -phobic coupling partners, provides a wide range of reactivity patterns. Analysis of the kinetic data shows that reactions with a hydrophobic catalyst are faster than with a hydrophilic catalyst. Diffusion-ordered spectroscopy experiments suggest compartmentalization of the hydrophobic catalyst inside micelles while the hydrophilic catalyst remains in the bulk aqueous phase. The autocatalytic effects observed can be tuned by varying reactant structure and coupling a hydrophilic alkyne and hydrophobic azide results in a more pronounced autocatalytic effect. We propose and test a model that rationalizes the observations in terms of the phase behavior of the reaction components and catalysts.
