2'-Hydroxyl-3phenyl propiophenone compound and preparation method and application thereof

A technology of phenylpropiophenone and compounds, applied in the field of 2'-hydroxy-3 phenylpropiophenone compounds and their preparation, can solve the problems of poor curative effect, cholinergic side effects, and butyrylcholinesterase inhibitory activity Bad question

Active Publication Date: 2019-09-24
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Patent literature discloses scutellarin aglycone carbamate derivatives (CN10337956A, CN102603698A), stilbene or ethane carbamate compounds (CN102816090A), isoflavone carbamate compounds (CN102827131A), ferulic acid Carbamate compounds (CN105837497A, CA105601540A, CN105646289A), chalcone compounds (CN105439876B, CN105481706B, CN105481796B), although these compounds have good acetylcholinesterase inhibitory activity and antioxidant activity, but for butyrylcholinesterase The inhibitory activity

Method used

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  • 2'-Hydroxyl-3phenyl propiophenone compound and preparation method and application thereof
  • 2'-Hydroxyl-3phenyl propiophenone compound and preparation method and application thereof
  • 2'-Hydroxyl-3phenyl propiophenone compound and preparation method and application thereof

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Embodiment 1

[0043] A kind of 2'-hydroxyl-3 phenyl propiophenone compound, its general chemical structure formula is as shown in (I):

[0044]

[0045] Among them, n, R 1 , R 2 See Table 1 for the definition.

[0046] Table 1 2'-hydroxyl-3 phenylpropiophenone compounds of the present invention

[0047]

[0048]

[0049]

[0050]

[0051] A kind of preparation method of 2'-hydroxyl-3 phenyl propiophenone compound, comprises the following steps:

[0052] (1) Add 2.0mmol of the corresponding 3-hydroxybenzaldehyde (1), 6.0mmol of dibromide (2), 4.0mmol of potassium carbonate and 15mL of acetonitrile into the reaction flask, heat to 65°C for 10 hours, and after the reaction, After conventional treatment, it was purified by silica gel column chromatography (eluent: petroleum ether: acetone = 50:1v / v) to obtain the corresponding alkoxybenzaldehyde (3);

[0053] (2) corresponding alkoxybenzaldehyde (3) 2.0mmol, secondary amine NR 1 R 2 (4) 2.5mmol and 3.0mmol of potassium carb...

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Abstract

The invention relates to a 2'-hydroxyl-3phenyl propiophenone compound and a preparation method and application thereof. The preparation method comprises the following steps that 1, 3-hydroxybenzaldehyde is used as an initial raw material, and under a first solvent and a first alkaline condition, the 3-hydroxybenzaldehyde reacts with dibromide to obtain bromine alkoxy benzaldehyde; 2, the bromine alkoxy benzaldehyde reacts with secondary amine under a second solvent and a second alkaline condition to obtain amine alkoxy benzaldehyde; 3, the amine alkoxy benzaldehyde and 2-hydroxyacetophenone react under a third solvent and a third alkaline condition to obtain amine alkoxy chalcone; 4, Pd/C is added to the amine alkoxy chalcone, and under the hydrogen atmosphere, under the condition of a fourth solvent, catalytic hydrogenation is conducted to obtain the 2'-hydroxyl-3phenyl propiophenone compound. The compound has obvious selective butyrycholine enzyme inhibition activity and can be applied to treatment and/or prevention of related neurodegeneration diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a 2'-hydroxyl-3-phenylpropiophenone compound and its preparation method and application. Background technique [0002] Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. The drugs currently approved by the FDA are mainly acetylch...

Claims

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Application Information

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IPC IPC(8): C07C217/22C07C217/58C07D219/10C07D295/088C07D295/096C07D211/14C07D217/04C07D491/20A61K31/138A61K31/473A61K31/495A61K31/4453A61K31/445A61K31/5375A61K31/472A61K31/55A61P25/00
CPCC07C217/22C07C217/58C07D219/10C07D295/088C07D295/096C07D211/14C07D217/04C07D491/20A61P25/00
Inventor 桑志培王柯人柳文敏时健程新峰于林涛
Owner NANYANG NORMAL UNIV
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