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

页码：275 / 286

页数：12

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