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Paper | Regular issue | Vol 91, No. 2, 2015, pp.275-286
Published online, 19th January, 2015
DOI: 10.3987/COM-14-13134
Synthesis, Characterization, and Biological Evaluation of Some Novel Glycosyl 1,3,4-Thiadiazole Derivatives as Acetylcholinesterase Inhibitors

Wei-wei Liu,* Qu-xiang Li, Da-hua Shi, Zhi-ling Cao, Feng-chang Cheng, Chuan-zhou Tao, Long Yin, and Xuan Wang

*School of Chemical Engineering, Huaihai Institute of Technology, Lianyungang City, Jiangsu Province 222005, China

Abstract

The corresponding 4-substituted glycosyl thiosemicarbazide derivatives (6a-6l) were obtained by the reaction of glycosyl isothiocyanate 4 with various hydrazides. Further cyclization with the system of p-TsCl/TEA led to the formation of N-glycosyl-5-substituted 1,3,4-thiadiazole-2-amine (7a-7l). Subsequent removal of the acetyl groups were conducted using the system of NaOMe/ MeOH. The chemical structures of all new products were confirmed by IR, 1H NMR and ESI-HRMS. The acetylcholinesterase (AChE) inhibitory activities of those compounds were tested by Ellman’s method. Among them, the compound 8h possessed the best acetylcholinesterase-inhibition activity with IC50 of 18.38 ± 0.89 µM.