Synthesis and bioactivity of novel C2-glycosyl oxadiazole derivatives as acetylcholinesterase inhibitors

Abstract

A series of glycosyl-substituted 1,3,4-oxadiazoles were synthesized by cyclization of glycosyl-acylthiosemicarbazides via a base-catalyzed reaction. The starting glycosyl-acylthiosemicarbazide derivatives were obtained by the reaction of glycosyl isothiocyanate with various hydrazides. The acetylcholinesterase (AChE) inhibitory activities of the products were tested by Ellman’s method. The most active compounds were subsequently evaluated for the 50% inhibitory concentration (IC50) values. N-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranosyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole-2-amine (6i) possesses the best AChE -inhibition activity with an IC50 of 1.61±0.34 μm.

Synthesis and anticholinesterase activities of novel glycosyl benzoxazole derivatives

“…3 Many studies have shown that glucosamine derivatives have strong biological properties, including antioxidant, anticancer, antibacterial, and anticholinesterase. 4–8…”

“…3 Many studies have shown that glucosamine derivatives have strong biological properties, including antioxidant, anticancer, antibacterial, and anticholinesterase. [4][5][6][7][8] Benzoxazole is a type of heterocyclic compound containing nitrogen and oxygen atoms. It has anti-inflammatory, anticancer, antibacterial, and plant virus killing activities, [8][9][10][11][12] and is widely used in medicine, pesticides, and biological fields.…”