1,2,4-triazole-3-thione derivative containing glucosamine molecule and its preparation method and use

A glucose and amino group-containing technology, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of complex and diverse pathogenesis, and achieve the effects of wide application prospects, cheap and easy-to-obtain raw materials, and convenient post-processing

Active Publication Date: 2018-08-24
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In recent years, the research on the pathogenesis of Alzheimer's disease has advanced by leaps and bounds, but the pathogenesis of AD is complex and diverse, which is caused by the joint action of many factors.

Method used

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  • 1,2,4-triazole-3-thione derivative containing glucosamine molecule and its preparation method and use
  • 1,2,4-triazole-3-thione derivative containing glucosamine molecule and its preparation method and use
  • 1,2,4-triazole-3-thione derivative containing glucosamine molecule and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Embodiment 1, a kind of 1,2,4-triazole-3-thione derivative containing glucosamine molecule, its molecular formula is as follows:

[0025]

[0026] Wherein, the R is selected from C 6 h 5 -, 4-CH 3 C 6 h 4 -, 4-CH 3 OC 6 h 4 -, 3-CH 3 OC 6 h 4 -, 4-FC 6 h 4 -, 4-ClC 6 h 4 -, 4-BrC 6 h 4 -, 4-IC 6 h 4 -, 4-NO 2 C 6 h 4 -, 3-NO 2 C 6 h 4 -, 2-FC 6 h 4 -, 2-ClC 6 h 4 -, 2-CH 3 C 6 h 4 -, 4-OHC 6 h 4 -, 3-NC 5 h 4 -, 4-N(CH 3 ) 2 C 6 h 4 -, 3-BrC 6 h 4 -, CH 3 -, C 4 h 3 S-, C 4 h 3 O-.

Embodiment 2

[0027] Embodiment 2, a method for synthesizing 1,2,4-triazole-3-thione derivatives containing glucosamine molecules as described in Example 1, the steps are as follows:

[0028] (1) Preparation of 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β-D-glucopyranose: 2-deoxy-2-amino-1 ,3,4,6-Tetra-O-benzyl- β -D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O- Benzyl- β -D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β - The molar ratio of D-pyranose hydrochloride to carbon disulfide, triethylamine and p-toluenesulfonyl chloride is 1:1:3:1, the reaction temperature is 0°C, and the reaction time is 1 hour.

[0029] (2) 4-(2-deoxy-1,3,4,6-tetra-O-benzyl- β -D-pyranose)-5-substituted-1,2,4-triazole-3-thione Preparation: 2-deoxy-2-isothiocyanate-1,3,4,6- Tetra-O-benzyl- β -D-Glucopyranose reacts with hydrazid...

Embodiment 3

[0030] Embodiment 3, a kind of synthetic method of the 1,2,4-triazole-3-thione derivative containing glucosamine molecule as described in embodiment 1, its steps are as follows:

[0031] (1) 2-Deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-glucopyranose preparation: 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β -D-pyranose hydrochloride, carbon disulfide and triethylamine are reacted, and then reacted with p-toluenesulfonyl chloride to obtain 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O- Benzyl- β -D-glucopyranose; reaction with acetonitrile as solvent, 2-deoxy-2-amino-1,3,4,6-tetra-O-benzyl- β - The molar ratio of D-pyranose hydrochloride to carbon disulfide, triethylamine and p-toluenesulfonyl chloride is 1:1.1:3.2:1.1, the reaction temperature is 0°C, and the reaction time is 1.5 hours.

[0032] (2) 4-(2-deoxy-1,3,4,6-tetra-O-benzyl- β -D-pyranose)-5-substituted-1,2,4-triazole-3-thione Preparation: 2-deoxy-2-isothiocyanate-1,3,4,6- Tetra-O-benzyl- β -D-Glucopyranose reac...

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Abstract

The invention relates to a 1,2,4-triazole-3-thioketone derivative containing glucosamine molecules. The invention further relates to a synthesizing method of the 1,2,4-triazole-3-thioketone derivative containing the glucosamine molecules. The method particularly comprises the following steps that 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose reacts with various substituted hydrazide, and by means of the action of a sodium hydroxide aqueous solution, 4-(2-deoxy-1,3,4,6-tetra-O-benzyl-beta-D-pyranose)-5-substituted-1,2,4-triazole-3-thioketone is generated through reacting. The synthesizing method has the advantages of being easy and safe to operate, small in environmental pollution, high in yield, simple in aftertreatment and the like. The synthesized compound has a high inhibiting effect on acetylcholinesterase and has a wide application prospect in preparing drugs for resisting acetylcholinesterase.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a 1,2,4-triazole-3-thione derivative containing glucosamine molecules, a preparation method thereof and an application as an acetylcholinesterase inhibitor. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease with insidious onset and progressive development, which is age-related and seriously affects the quality of life of the elderly. Vascular disease, cancer. At the same time, the disability rate of Alzheimer's disease is also high, and the clinical symptoms include: memory loss, cognitive dysfunction, abnormal behavior and social impairment. In recent years, the research on the pathogenesis of Alzheimer's disease has advanced by leaps and bounds, but the pathogenesis of AD is complex and diverse, which is caused by the joint action of many factors. At present, AChEI is the most widely used drug for treating AD clinically so far. Therefore...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/056C07H1/00A61K31/7056A61P25/28
CPCC07H1/00C07H19/056
Inventor 刘玮炜殷龙程峰昌史大华王蕾刘秀坚
Owner HUAIHAI INST OF TECH
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