5160-10-1Relevant articles and documents
Synthesis of C-Oligosaccharides through Versatile C(sp3)?H Glycosylation of Glycosides
Ackermann, Lutz,Kopp, Adelina,Wu, Jun
supporting information, (2022/02/01)
C-oligosaccharides are pharmacologically relevant because they are more hydrolysis-resistant than O-oligosaccharides. Despite indisputable advances, C-oligosaccharides continue to be underdeveloped, likely due to a lack of efficient and selective strategies for the assembly of the interglycosidic C?C linkages. In contrast, we, herein, report a versatile and robust strategy for the synthesis of structurally complex C-oligosaccharides via catalyzed C(sp3)?H activations. Thus, a wealth of complex interglycosidic (2→1)- and (1→1)-C-oligosaccharides becomes readily available by palladium-catalyzed C(sp3)?H glycoside glycosylation. The isolation of key palladacycle intermediates and experiments with isotopically-labeled compounds identified a trans-stereoselectivity for the C(sp3)?H glycosylation. The glycoside C(sp3)?H activation manifold was likewise exploited for the diversification of furanoses, pyranoses and disaccharides.
Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity
Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder
, (2021/11/23)
Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.
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.
