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

A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and...

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Published in:Journal of chemical research 2019-07, Vol.43 (7-8), p.257-261
Main Authors: Wang, Lei, Wu, Yu-Ran, Ren, Shu-Ting, Yin, Long, Wang, You-Xian, Liu, Shu-Hao, Liu, Wei-Wei, Shi, Da-Hua, Cao, Zhi-Ling, Sun, Hui-Min
Format: Article
Language:English
Subjects:
Alcohol
Chromatography
Derivatives
NMR
Nuclear magnetic resonance
Thioureas
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Summary:A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and the glycosyl thiourea was prepared through a series of steps from D-Glucosamine. The acetylcholinesterase-inhibitory activities of the products were tested by Ellman’s method. The most active compounds were subsequently evaluated for the 50% inhibitory concentration values. N-(1,3,4,6-tetra-O-benzyl-2-deoxy-β-D-glucopyranosyl)-4-(5-methoxy-benzofuran-2-yl)-1,3-thiazole-2-amine possessed the best acetylcholinesterase-inhibition activity with a 50% inhibitory concentration of 2.03 ± 0.26 μM.
ISSN:1747-5198
2047-6507
DOI:10.1177/1747519819856973