Synthesis and biological evaluation of novel C1-glycosyl thiazole derivatives as acetylcholinesterase inhibitors

A new series of C1-glycosyl thiazole derivatives was synthesised by the reaction of 1-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea with 2-bromoacetophenone derivatives. Subsequent removal of the acetyl groups were conducted using NaOMe–MeOH. The structures of all new products were...

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Bibliographic Details
Published in:Journal of chemical research 2016-09, Vol.40 (9), p.545-548
Main Authors: Yin, Long, Cheng, Feng–Chang, Li, Qu–Xiang, Liu, Wei–Wei, Liu, Xiu–Jian, Cao, Zhi–Ling, Shi, Da–Hua
Format: Article
Language:English
Subjects:
Derivatives
Inhibition
Inhibitors
Nuclear magnetic resonance
Synthesis
Ureas
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Summary:A new series of C1-glycosyl thiazole derivatives was synthesised by the reaction of 1-(1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranos-2-yl)thiourea with 2-bromoacetophenone derivatives. Subsequent removal of the acetyl groups were conducted using NaOMe–MeOH. The structures of all new products were confirmed by IR, 1H NMR and HRMS (ESI). The acetylcholinesterase inhibitory activities of these new compounds were tested. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(4-nitrophenyl)-1,3-thiazole-2-amine showed the best activity with an inhibition rate of 43.21%.
ISSN:1747-5198
2047-6507
DOI:10.3184/174751916X14711768865726