2-hydroxychalcone amine compounds and application thereof

一种羟基查尔酮胺、化合物的技术，应用在一类2‑羟基查尔酮胺类化合物及其用途领域，能够解决解聚活性不理想、疗效欠佳等问题

Inactive Publication Date: 2018-02-16
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the previous research, we designed and synthesized scutellarin aglycon carbamate derivatives (CN101337956A, CN102603698A), stilbene or ethane carbamate for the acetylcholinesterase and oxidative stress factors in the pathogenesis of AD Ester compounds (CN102816090A), isoflavone carbamate compounds (CN102827131A), flavonoid alkylamine compounds (CN103087024A), genistein alkylamine compounds (CN103113340A), stilbene oxyalkylamine compounds (CN103073440A), although these compounds have good acetylcholinesterase inhibitory and antioxidant activities, but for A β 1-42 Inhibition of self-aggregation (inhibition rates of less than 65.0% at 20.0 µM concentration), Cu 2+ Induced A β 1-42 Inhibition of aggregation (inhibition rates of less than 65.0% at a concentration of 20.0 µM) and 2+ Induced A β 1-42 The aggregation disaggregation activity (the disaggregation rate is less than 60.0% at the concentration of 20.0µM) is not satisfactory, resulting in the poor efficacy of these compounds on AD in animal models

Method used

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  • 2-hydroxychalcone amine compounds and application thereof
  • 2-hydroxychalcone amine compounds and application thereof
  • 2-hydroxychalcone amine compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 General method for the preparation of 2-hydroxychalcone amines (I)

[0038] Add 2.0 mmol of the corresponding 2-hydroxyacetophenone compound (2), 3.0 mmol of the corresponding benzaldehyde compound (1) and 30 ml of ethanol into the reaction flask, stir well, then add 12.0 mmol of 30% KOH aqueous solution dropwise, Stir and react at 40-50°C for 2.0 to 72.0 hours (the reaction progress 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, and then adjust the pH of the reaction solution with saturated sodium bicarbonate aqueous solution To weak alkalinity, evaporate ethanol under reduced pressure, add 100 mL deionized water to the residual liquid, extract three times with 300 mL dichloromethane, combine organic layers, wash with saturated aqueous sodium chloride solution, and dry over anhydrous sodium sulfate Filtrate, evaporate the solvent under redu...

Embodiment 2

[0063] Example 2 General method for the preparation of 2-hydroxychalcone amine compound (I) and acid salt formation

[0064] Add 2.0 mmol of 2-hydroxychalcone amine compound (I) obtained according to the above Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, heat and reflux and stir for 20 minutes, and the reaction is over 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 2-hydroxychalcone amine compound (I). 1 Confirmed by H NMR and ESI-MS.

Embodiment 3

[0065] Example 3 Screening results of biological activity of some 2-hydroxychalcone amine compounds (I)

[0066] .

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Abstract

The invention discloses a kind of 2-hydroxychalcone amine compounds (I) and pharmaceutically acceptable salts, pharmaceutical compositions, and application of 2-hydroxychalcone amine compounds (I) andpharmaceutically acceptable salts to prepare medicines for treating and / or preventing and controlling neurodegenerative 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.

Description

[0001] related application [0002] This application is a divisional application, the application number of the original application is 201410478475.1, the application date is September 19, 2014, and the invention name is "2-hydroxychalcone amine compounds, their preparation method and use". technical field [0003] The invention belongs to the field of medicinal chemistry and relates to a novel 2-hydroxychalcone amine compound (I) and a pharmaceutically acceptable salt thereof, a preparation method, a pharmaceutical composition and a preparation method for treating and / or preventing neurodegeneration Sex-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, neurological Pain, glaucoma and other neurodegenerative diseases. Background technique [0004] Alzheimer's disease (Alzheimer's disease, AD, senile dementia) is a degenera...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/22A61K31/445A61P25/28A61P25/16A61P25/14A61P25/04A61P21/00A61P27/06
CPCC07D211/22
Inventor 邓勇谭正怀桑志培强晓明李岩
Owner SICHUAN UNIV
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