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

Heterocyclic communications

article

Lei Wang¹  Hui-Min Sun¹  Yu-Ran Wu¹  Shu-Ting Ren¹  Long Yin¹  Xiu-Jian Liu¹  Feng-Chang Cheng²  Wei-Wei Liu¹  Da-Hua Shi¹  Zhi-Ling Cao¹ 

[1]College of Pharmaceutical Sciences, Huaihai Institute of Technology

[2]China University of Mining and Technology

[3]Jiangsu Institute of Marine Resources

[4]Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, Huaihai Institute of Technology

[5]Co-Innovation Center of Jiangsu Marine Bio-industry Technology

关键词: Acetylcholinesterase inhibitors;    glycosyl 1;    3;    4-oxadiazoles;    synthesis;   

DOI  :  10.1515/hc-2018-0166

学科分类：内科医学

来源: De Gruyter

【 摘 要 】

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 (IC 50 ) 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 IC 50 of 1.61±0.34 μ m .

【 授权许可】

CC BY|CC BY-NC-ND