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Thiazole derivative containing aminoglucose and coumarin and preparation method and uses thereof

A technology of glucosamine and coumarin, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of cognitive decline and memory loss in AD patients, and achieves widening the scope of application and strong inhibition. Active, biologically active effects

Active Publication Date: 2018-11-09
HUAIHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Deficiency of acetylcholine leads to cognitive decline and loss of memory in AD patients

Method used

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  • Thiazole derivative containing aminoglucose and coumarin and preparation method and uses thereof
  • Thiazole derivative containing aminoglucose and coumarin and preparation method and uses thereof
  • Thiazole derivative containing aminoglucose and coumarin and preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1, a kind of thiazole derivative containing glucosamine and coumarin molecules, its molecular formula is as follows:

[0027]

[0028] Wherein, the R is selected from H-; 6-CH 3 -6-OCH 3 -8-OCH 3 -;6,8-Br 2 -;6-NO 2 -; 6-Cl-; 6-Br-; 6-F-; 8-OC 2 h 5 - 7-OCH 3 -; 6-I-; 5-F-; 8-NO 2 -;6,8-Cl 2 -;6,8-I 2 -; 5-F-; 6-Cl-8-Br-.

Embodiment 2

[0029] Embodiment 2, a kind of synthetic method of the thiazole derivative containing amino sugar and coumarin molecule as described in embodiment 1, its steps are as follows:

[0030] (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 1:1:3:1, 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)thiourea preparation: in 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-Glucopyranose is passed into ammonia gas, and ...

Embodiment 3

[0033] Embodiment 3, a kind of synthetic method of the thiazole derivative containing glucosamine and coumarin molecule as described in embodiment 1, its steps are as follows:

[0034] (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 1:1.3:3.5:1.3, 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)thiourea preparation: in 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl- β -D-Glucopyranose is passed into ammonia ga...

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Abstract

The invention relates to a thiazole derivative containing aminoglucose and coumarin, and also relates to a synthetic method of the derivative. The method includes: firstly reacting 2-deoxy-2-isothiocyanate-1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose with ammonia gas to synthesize an intermediate that is glycosyl thiourea; and then reacting the glycosyl thiourea with a substituted 3-(bromoacetyl) coumarin derivative to synthesize N-(1,3,4,6-tetra-O-benzyl-beta-D-glucopyranose-2-yl)-4-(substituted coumarin-3-yl)-1,3-thiazole-2-amine. The method is simple and safe to operate, low in environment pollution, high in yield, and simple in after-treatment. The synthesized thiazole derivative has high suppression function on acetylcholin esterase, and has a wide application prospect in the field ofpreparing anti-(acetylcholin esterase) medicines.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a thiazole derivative containing glucosamine and coumarin molecules, a preparation method thereof and an application as an acetylcholinesterase inhibitor. Background technique [0002] With the acceleration of population aging, Alzheimer's disease (AD) has become one of the important killers threatening human health. The occurrence and development of AD is closely related to the growth of age. Studies have shown that the prevalence of AD in the elderly aged 60-64 is 0.39%, and the prevalence of AD in the elderly after the age of 90 is as high as 10.48%. The main clinical manifestations are deteriorating cognition and memory function, progressive decline in daily life ability, accompanied by various neuropsychiatric symptoms and behavioral disturbances. At present, the more accepted pathology of AD in the world is "cholinergic deficiency theory". According to the theory, the ...

Claims

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Application Information

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IPC IPC(8): C07H17/00C07H1/00A61P25/28
CPCA61P25/28C07H1/00C07H17/00
Inventor 刘玮炜刘秀坚王蕾殷龙吴煜然任抒婷王有宪刘书豪曹志凌史大华
Owner HUAIHAI INST OF TECH
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