2-hydroxychalcone amine compounds, and preparation method and uses thereof

A technology of hydroxychalcone amines and compounds, which is applied in the field of 2-hydroxychalcone amines, their preparation and application, and can solve the problems of poor curative effect and unsatisfactory depolymerization activity, etc.

Inactive Publication Date: 2016-03-30
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 rate at 20.0μM concentration is less than 65.0%), for Cu 2+ Induced A β 1-42 Inhibition of aggregation (inhibition rate at 20.0μM concentration is less than 65.0%) and the effect on Cu 2+ Induced A β 1-42 The aggregation disaggregation activity (the disaggregation rate at 20.0μM concentration is less than 60.0%) is not ideal, resulting in poor efficacy of these compounds on AD in animal models

Method used

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  • 2-hydroxychalcone amine compounds, and preparation method and uses thereof
  • 2-hydroxychalcone amine compounds, and preparation method and uses thereof
  • 2-hydroxychalcone amine compounds, and preparation method and uses thereof

Examples

Experimental program
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Effect test

Embodiment 12

[0035] General method for the preparation of embodiment 12-hydroxychalcone amine compound (I)

[0036] Add 2.0mmol corresponding 2-hydroxyacetophenone compound ( 2 ), 3.0mmol corresponding benzaldehyde compounds ( 1 ) and 30ml ethanol, after stirring evenly, add 12.0mmol of 30% KOH aqueous solution dropwise, and stir at 40-50°C for 2.0-72.0 hours (reaction progress is tracked by TLC); after the reaction, cool to room temperature and adjust with 10% hydrochloric acid aqueous solution The pH of the reaction solution was strongly acidic, and the pH of the reaction solution was adjusted to weak alkalinity with saturated aqueous sodium bicarbonate solution, and the ethanol was evaporated under reduced pressure, and 100 mL of deionized water was added to the residual liquid, extracted three times with 300 mL of dichloromethane, and the organic layers were combined Afterwards, it was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and f...

Embodiment 22

[0060] Example 22- General method for preparation of hydroxychalcone amine compound (I) and acid salt formation

[0061] In the reaction flask, add the 2-hydroxychalcone amine compound ( I ) 2.0mmol and 50ml of acetone, after stirring evenly, add 8.0mmol of the corresponding acid, heat up and reflux and stir for 20 minutes, cool to room temperature after the reaction, evaporate the solvent under reduced pressure, recrystallize the residue with acetone, filter the precipitated solid, that is Obtain 2-hydroxychalcone amine compound ( I ) of the salt, its chemical structure by 1 Confirmed by HNMR and ESI-MS.

Embodiment 3

[0062] Example 3 Part 2-Hydroxychalcone amine compound (I) biological activity screening results

[0063] .

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Abstract

The invention discloses 2-hydroxychalcone amine compounds and pharmaceutically-acceptable salts, preparation method thereof, pharmaceutical composition, and uses for preparing medicines treating and/or preventing neurodegenerative related diseases, the diseases including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntingdon's disease, HIV associated dementia, multiple sclerosis, progressive lateral sclerosis, neuropathic pain, glaucoma and other neurodegenerative diseases.

Description

technical field [0001] 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 [0002] Alzheimer's disease (AD, senile dementia) is a degenerative disease of the central nervous system mainly characterized by progressive cognitive impairment and memory impairment. The high incidence of cardiovascular disease and cancer has risen to the fourth cause of death in developed countries such as Europe and the United States. According to the report of the World...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C217/20C07C213/00C07D219/10C07D295/088C07D211/14C07D491/107C07C225/22C07C221/00C07D295/112C07D211/22A61K31/138A61K31/473A61K31/495A61K31/4453A61K31/5375A61K31/445A61K31/40A61K31/55A61P25/28A61P25/14A61P25/16A61P31/18A61P25/00A61P25/04A61P27/06
CPCC07D211/22
Inventor 邓勇谭正怀桑志培强晓明李岩
Owner SICHUAN UNIV
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