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Benzisoselenazolone quinoline derivative and application thereof in treatment of Alzheimer's disease

A technology of compounds and hydrates, which is applied in the field of medicine, can solve the problems of no new drugs being successfully marketed and no breakthroughs, etc., to achieve the ability to inhibit metal ion chelation, inhibit Aβ aggregation, and excellently simulate glutathione process. Effect of oxidase activity

Inactive Publication Date: 2017-01-04
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past two decades, the development of anti-AD drugs aimed at inhibiting Aβ aggregation or clearing senile plaques formed by Aβ aggregation, or targeting other single targets, has been a hot spot in this field, but so far, no breakthroughs have been made , no new drug was successfully marketed

Method used

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  • Benzisoselenazolone quinoline derivative and application thereof in treatment of Alzheimer's disease
  • Benzisoselenazolone quinoline derivative and application thereof in treatment of Alzheimer's disease
  • Benzisoselenazolone quinoline derivative and application thereof in treatment of Alzheimer's disease

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1 5-nitro-7-chloro-8-hydroxyquinoline

[0024]

[0025] 5-Nitro-8-hydroxyquinoline (4.8g, 25.2mmol) and KOH solution (1mol / L, 25.2mL) were added to 480mL deionized water, and NaClO solution (7%, 34.2mL ). During the dropwise addition, the raw material was completely dissolved, and then a solid precipitated out. Acetic acid was added dropwise to adjust the solution to pH=6. Suction filtration and vacuum drying yielded 4.0 g of a yellow solid. Melting point, 239°C. Yield 71%

Embodiment 2

[0026] Example 2 5-nitro-7-iodo-8-hydroxyquinoline

[0027]

[0028] 5-Nitro-8-hydroxyquinoline (10.0g, 52.6mmol) and KOH (9g, 160.0mmol) were added to 1000mL deionized water, and evenly mixed I 2 (13.35g, 52.6mmol) and KI (8.73g, 52.6mmol) were solid. After stirring at room temperature for 2h, acetic acid was added dropwise to adjust the solution to pH=6. Suction filtration and vacuum drying yielded 10.8 g of a yellow solid. Melting point, 236°C. Yield 65%

Embodiment 3

[0029] Example 3 tert-butyl-(5-nitro-8-hydroxyquinoline) carbonate

[0030]

[0031] Dissolve 5-nitro-8-hydroxyquinoline (10.0g, 52.6mmol) and di-tert-butyl carbonate (12.7g, 57.8mmol) in n-hexane / dichloromethane (420mL, V / V=1:2) 4-N,N-dimethylaminopyridine (0.65 g, 5.26 mmol) and diisopropylethylamine (11.2 mL, 63.12 mmol) were added under stirring at room temperature. After stirring for 14h, it was filtered with suction and concentrated. Purified by column chromatography to obtain 14.0 g of light yellow solid. Yield 92%. 1 H NMR (400MHz, CDCl 3 )δ9.06(d, J=8.9Hz, 1H), 9.03(s, 1H), 8.44(d, J=8.4Hz, 1H), 7.68(dd, J=5.5, 3.3Hz, 1H), 7.62( d, J=8.4Hz, 1H), 1.60(s, 19H).

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PUM

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Abstract

The invention provides a benzisoselenazolone quinoline derivative as shown in a formula I, or pharmaceutically acceptable salts, hydrate, solvates, crystal-form isomers or diastereoisomers thereof, as well as an application of compounds or compositions in medicines for treatment, improvement and / or prevention of an Alzheimer's disease. Experiments prove that the benzisoselenazolone quinoline derivative disclosed by the invention has excellent capacity of simulating glutathione peroxidase activity and restraining A beta aggregation and metal ion chelation, and is a multi-target Alzheimer's disease resistant active molecule. The benzisoselenazolone quinoline derivative is as shown in the formula I, wherein R1, R2, R3, R4 and X in the formula I are defined as the description.

Description

technical field [0001] The invention belongs to the technical field of medicine, and mainly relates to benzisoselazolone quinoline derivatives and their application in treating, improving and / or preventing anti-Alzheimer's disease. Background technique [0002] Alzheimer's disease (AD), also known as primary senile dementia (senile dementia), is a degenerative disease of the central nervous system with memory loss and cognitive dysfunction as the main clinical manifestations. According to statistics, there are more than 30 million AD patients in the world, with 4.6 million new cases every year. It is estimated that by 2050, this number will exceed 100 million. At present, the number of AD patients in my country is about 6 million, and it is predicted that it will increase to 10 million by 2025, ranking first in the world. With the continuous extension of human life span and aging population, AD has become one of the most serious diseases threatening human health, along with...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D421/04A61K31/4709A61P25/28
CPCC07D421/04
Inventor 黄玲王志仁王亚丽黎兴术
Owner SUN YAT SEN UNIV
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