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Glucosamine-containing 1,3,4-thiadiazole derivative, and preparation method and application thereof

A technology of thiadiazole derivatives and glucose, which is applied in the field of drug preparation, can solve problems such as narrow therapeutic range, poor drug selectivity, and large gastrointestinal irritating side effects

Active Publication Date: 2015-12-02
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the existing AChE inhibitors have become the mainstream drugs for the treatment of AD, the existing AChE inhibitors generally have poor drug selectivity, low bioavailability, large gastrointestinal irritating side effects, narrow therapeutic range, and severe liver cell damage. Disadvantages such as toxicity

Method used

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  • Glucosamine-containing 1,3,4-thiadiazole derivative, and preparation method and application thereof
  • Glucosamine-containing 1,3,4-thiadiazole derivative, and preparation method and application thereof
  • Glucosamine-containing 1,3,4-thiadiazole derivative, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, a kind of 1,3,4-thiadiazole derivatives containing glucosamine, its molecular formula is as follows:

[0027]

[0028] Wherein, the R is selected from C 9 h 19 -,C 6 h 5 -,2-CH 3 C 6 h 4 -,3-CH 3 C 6 h 4 -,4-CH 3 C 6 h 4 -,4-CH 3 OC 6 h 4 -,2-CH 3 OC 6 h 4 -,3-NO 2 C 6 h 4 -,4-NO 2 C 6 h 4 -,2-OHC 6 h 4 -,3-OHC 6 h 4 -,4-OHC 6 h 4 -,3-BrC 6 h 4 -,4-BrC 6 h 4 -,3-ClC 6 h 4 -,4-ClC 6 h 4 -,3-FC 6 h 4 -,4-FC 6 h 4 -,2,3-Cl 2 C 6 h 3 -,2,4-Cl 2 C 6 h 3 -,C 10 h 7 -.

Embodiment 2

[0029] Embodiment 2, a kind of synthetic method containing glucosamine 1,3,4-thiadiazole derivative as described in embodiment 1, its steps are as follows:

[0030] (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.

[0031] (2) N-(1,3,4,6-tetra-O-benzyl-2-deoxy- β -D-glucopyranose-2-yl)-N'-thiosemicarbazide preparation: 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β- The reaction of D-glucopyranose with hydrazine hydrate give...

Embodiment 3

[0033] Embodiment 3, a kind of synthetic method containing glucosamine 1,3,4-thiadiazole derivative as described in embodiment 1, its steps are as follows:

[0034] (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 1:1.2:3.5:1.2, the reaction temperature is 0°C, and the reaction time is 2 hours.

[0035] (2) N-(1,3,4,6-tetra-O-benzyl-2-deoxy- β -D-glucopyranose-2-yl)-N'-thiosemicarbazide preparation: 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-β- The reaction of D-glucopyranose with hydrazine hydra...

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Abstract

The invention relates to a glucosamine-containing 1,3,4-thiadiazole derivative and a synthesis method of the lucosamine-containing 1,3,4-thiadiazole derivative. The method comprises the following steps: reacting 2-desoxy-2-isorhodanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose with hydrazine hydrate to synthesize an intermediate glycosyl thiosemicarbazide, and reacting with substituted aldehyde and a Fe<3+> compound to synthesize the N-(5-substituted-1,3,4-thiadiazolyl-2-yl)-1,3,4,6-tetra-O-benzyl-2-desoxy-beta-D-glucosamine. The synthesis method is simple and safe to operate, and has the advantages of small environmental pollution, high yield and simple after-treatment. The synthesized compound has a strong inhibiting effect on acetylcholinesterase, and has wide application prospects in the aspect of preparation of anti-acetylcholinesterase drugs.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a glucosamine-containing 1,3,4-thiadiazole derivative, a preparation method thereof and an application as an acetylcholinesterase inhibitor. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD) is a kind of central nervous system degenerative disease mainly characterized by acquired memory loss and cognitive dysfunction. Clinical symptoms include: cognitive impairment, memory impairment, time and Spatial orientation disorder, withdrawn and indifferent personality, mental behavior disorder, etc. According to the estimates of the International Alzheimer's Association, there were about 36 million dementia patients in the world in 2010, and it is estimated that the number of dementia patients will reach 115 million by 2050. In my country, AD will seriously affect the quality of life of the elderly. The total prevalence of AD in the elderly over 65 years old...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00A61P25/28
Inventor 刘玮炜程峰昌殷龙史大华
Owner HUAIHAI INST OF TECH
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