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Aurone mannich base compound and preparation method and application thereof

A technology of aurone Mannich base and aurome Mannich base, which is applied in the field of aurone Mannich base compounds, their preparation and application, and can solve the problems of poor curative effect and weak inhibitory activity, etc.

Active Publication Date: 2017-05-10
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In previous studies, we focused on the oxidative stress, β -A class of 4-hydroxyaurone compounds (CN 105646417A) was designed and synthesized due to factors such as excessive generation and deposition of amyloid protein and metabolic disorders of metal ions. The results of biological activity tests showed that these compounds not only have good monoamine oxidase activity- B inhibitory activity against A β 1-42 self-aggregation and Cu 2+ Induced A β 1-42 Aggregation also has strong inhibitory activity, and also has strong anti-oxidative stress and metal ion complexation, but the inhibitory activity of this type of compound on acetylcholinesterase is weak (the inhibition rate at 50.0 μM concentration is less than 50.0% ), resulting in poor curative effect of these compounds on AD in animal models; and acetylcholinesterase inhibitors are currently the most widely used clinically used drugs for the treatment of AD. The effect of symptoms is clear

Method used

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  • Aurone mannich base compound and preparation method and application thereof
  • Aurone mannich base compound and preparation method and application thereof
  • Aurone mannich base compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 General method for the preparation of auran Mannich base compound (I)

[0033] Add 2.0 mmol of the corresponding benzofuran-3 ( 2H )-Ketone compound (1), 3.0 mmol of the corresponding hydroxybenzaldehyde Mannich base compound (2) and 30 ml of ethanol. After stirring well, 12.0 mmol of 30% KOH aqueous solution was added dropwise, and the reaction was stirred at room temperature for 3.0-40.0 hours (The reaction process is tracked by TLC); after the reaction, cool to room temperature, adjust the pH of the reaction solution to strong acidity with 10% aqueous hydrochloric acid, then adjust the pH of the reaction solution to weakly alkaline with saturated aqueous sodium bicarbonate solution, and distill off the ethanol under reduced pressure 80 mL of deionized water was added to the remaining solution, and then extracted three times with 240 mL of dichloromethane. The organic layers were combined and washed with saturated aqueous sodium chloride solution, dried over anh...

Embodiment 2

[0040] Example 2 General method for preparing salt of auran Mannich base compound (I) and acid

[0041] Add 2.0 mmol of the auran Mannich base compound (I) obtained in Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, and react at reflux with heating for 20 minutes. After the reaction is complete After cooling to room temperature, the solvent was evaporated under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain the salt of auran Mannich base compound (I). Its chemical structure was 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses an aurone mannich base compound and pharmaceutically acceptable salts, a preparation method, a pharmaceutical composition and application thereof in preparation of medicines for treatment and / or prevention of neurodegeneration related diseases. The neurodegeneration related diseases include but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related dementia, multiple sclerosis, progressive lateral sclerosis of spinal cord, neuropathic pain, glaucoma and the like.

Description

Technical field [0001] The present invention belongs to the field of medicinal chemistry, and relates to a new type of auran Mannich base compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation for the treatment and / or prevention of neurodegeneration Use in drugs for related diseases, including but not limited to vascular dementia, Alzheimer’s disease, Parkinson’s disease, Huntington’s disease, HIV-related dementia, multiple sclerosis, progressive lateral spinal sclerosis, neuropathic pain , Glaucoma and other neurodegenerative diseases. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD, Alzheimer's disease) is a central nervous system degenerative disease dominated by progressive cognitive impairment and memory impairment. Its incidence is increasing year by year, becoming second only to the heart. The high incidence of vascular disease and cancer has risen to the fourth cause of death in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/83A61K31/343A61K31/4025A61K31/5377A61K31/496A61K31/443A61P25/28A61P25/16A61P25/14A61P31/18A61P25/00A61P27/06
CPCC07D307/83
Inventor 邓勇李岩强晓明曹忠诚郑云小竹徐锐宋青
Owner SICHUAN UNIV
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