Synthesis and anti-acetylcholinesterase activities of novel glycosyl coumarylthiazole derivatives

Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR...

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Bibliographic Details
Published in:Journal of chemical research 2021-05, Vol.45 (5-6), p.359-364
Main Authors: Wang, You-Xian, Liu, Shu-Hao, Shao, Zhong-Bai, Cao, Lian-Gong, Jiang, Kai-Jun, Lu, Xing, Wang, Lei, Liu, Wei-Wei, Shi, Da-Hua, Cao, Zhi-Ling
Format: Article
Language:English
Subjects:
Condensates
Ethanol
NMR
Nuclear magnetic resonance
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Summary:Eleven glycosyl coumarylthiazole derivatives are synthesized by cyclization and condensation of glycosyl thiourea with 3-bromoacetyl coumarins in ethanol. The reaction conditions are optimized and good yields of products (80%–95%) are obtained. The structures of all new products were confirmed by IR, 1H and 13C NMR, and by HRMS (electrospray ionization). The in vitro acetylcholinesterase (AChE) inhibitory activities of these new compounds are tested by Ellman’s method. Among them, N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4-(6-nitrocoumarinyl)-1,3-thiazole-2-amine showed the best activity with an in vitro AChE inhibitory rate of 58% and an IC50 value of 12 ± 0.38 μg/mL.
ISSN:1747-5198
2047-6507
DOI:10.1177/1747519820948358