SYNTHESIS, CHARACTERIZATION, AND BIOLOGICAL EVALUATION OF SOME NOVEL GLYCOSYL 1,3,4-THIADIAZOLE DERIVATIVES AS ACETYLCHOLINESTERASE INHIBITORS

被引：11
作者：
Liu, Wei-wei [1 ,2 ,3 ]
Li, Qu-xiang [2 ]
Shi, Da-hua [1 ,3 ]
Cao, Zhi-ling [1 ,3 ]
Cheng, Feng-chang
Tao, Chuan-zhou [1 ,3 ]
Yin, Long [1 ]
Wang, Xuan [1 ]
机构：
[1] Huaihai Inst Technol, Sch Chem Engn, Lianyungang 222005, Peoples R China
[2] China Univ Min & Technol, Xuzhou 221116, Peoples R China
[3] Jiangsu Marine Resources Dev Res Inst, Lianyungang 222005, Peoples R China
来源：
HETEROCYCLES | 2015年 / 91卷 / 02期
关键词：
D-Glucosamine; 1,3,4-Thiadiazole; Acetylcholinesterase Inhibitor; POTENTIAL ANTIBACTERIAL; ANTIDEPRESSANT; ANALOGS;
D O I：
10.3987/COM-14-13134
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The corresponding 4-substituted glycosyl thiosemicarbazide derivatives (6a-61) 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-71). Subsequent removal of the acetyl groups were conducted using the system of NaOMe/MeOH. The chemical structures of all new products were confirmed by JR. H-1 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 mu M.
引用
收藏
页码：275 / 286
页数：12
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