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Aurone Mannich base compound, its preparation method and use

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 weak inhibitory activity and poor curative effect

Active Publication Date: 2019-03-19
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, its preparation method and use
  • Aurone Mannich base compound, its preparation method and use
  • Aurone Mannich base compound, its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1 General method for the preparation of aurone 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 evenly, add 12.0 mmol of 30% KOH aqueous solution dropwise, and stir at room temperature for 3.0 to 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% hydrochloric acid aqueous solution, then adjust the pH of the reaction solution to weak alkalinity with saturated aqueous sodium bicarbonate solution, and distill off ethanol under reduced pressure , 80 mL of deionized water was added to the residual liquid, extracted three times with 240 mL of dichloromethane, the organic layers were combined and washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulf...

Embodiment 2

[0041] Example 2 General method for the preparation of aurone Mannich base compound (I) and acid salt formation

[0042] Add 2.0 mmol of the aureus-Mannich base compound (I) obtained according to the above-mentioned Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, heat up and reflux and stir for 20 minutes, after the reaction is completed Cool to room temperature, distill the solvent off under reduced pressure, recrystallize the residue with acetone, filter the precipitated solid to obtain the salt of the aureus Mannich base compound (I), its chemical structure has been confirmed by 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 invention belongs to the field of medicinal chemistry, and relates to a new type of aurone-Mannich base compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation for treating and / or preventing neurodegeneration Use in medicines 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 sclerosis, neuropathic pain , glaucoma and other neurodegenerative diseases. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD, senile dementia) is a degenerative disease of the central nervous system mainly characterized by progressive cognitive impairment and memory impairment. Vascular diseases and cancers are high-incidence diseases, which have risen to the fourth cause of death in developed countries such as Europe and the United States. ...

Claims

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Application Information

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Patent Type & Authority Patents(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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