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Carbamate chalcone compound, preparation method therefor and use of carbamate chalcone compound

A technology of chalcone ester and carbamic acid, which is applied in the field of medicinal chemistry of the Ming Dynasty, and can solve problems such as unsatisfactory depolymerization activity and poor curative effect

Inactive Publication Date: 2016-04-13
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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), although these compounds have good acetylcholinesterase inhibitory and antioxidant activity, but for A β 1-42 Inhibition of self-aggregation (inhibition rate at 25.0μM concentration is less than 30.0%), for Cu 2+ Induced A β 1-42 Inhibition of aggregation (inhibition rate at 25.0μM concentration is less than 35.0%) and on Cu 2+ Induced A β 1-42 The aggregation disaggregation activity (the disaggregation rate at 25.0μM concentration is less than 35.0%) is not ideal, resulting in poor efficacy of these compounds on AD in animal models

Method used

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  • Carbamate chalcone compound, preparation method therefor and use of carbamate chalcone compound
  • Carbamate chalcone compound, preparation method therefor and use of carbamate chalcone compound
  • Carbamate chalcone compound, preparation method therefor and use of carbamate chalcone compound

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Embodiment 1

[0047] The preparation general method of embodiment 1 carbamic acid chalcone ester compound (I)

[0048] Add 2.0mmol corresponding 2-hydroxyacetophenone compound ( 2 ), 3.0mmol corresponding benzaldehyde compounds ( 1 ), 8.0mmol of anhydrous potassium carbonate and 50ml of acetonitrile, after stirring evenly, the temperature was raised to reflux and stirred for 2.0 to 72.0 hours (the reaction process was tracked by TLC); after the reaction was completed, it was cooled to room temperature, and the pH of the reaction solution was adjusted with 10% hydrochloric acid aqueous solution to Strong acidity, then use saturated aqueous sodium bicarbonate solution to adjust the pH of the reaction solution to weak alkalinity, evaporate acetonitrile under reduced pressure, add 80mL deionized water to the residual liquid, extract three times with 300mL dichloromethane, combine the organic layers with saturated chlorine Wash with aqueous sodium chloride solution, dry over anhydrous sodium ...

Embodiment 2

[0058] General method for the preparation of embodiment 2 carbamic acid chalcone ester compound (I)

[0059] Add 2.0mmol corresponding 2-hydroxyacetophenone compound ( 4 ) or dihydroxyacetophenones ( 9 ), 3.0mmol corresponding hydroxybenzaldehyde compounds ( 3 ) or benzaldehyde compounds ( 8 ), and 40ml ethanol, after stirring evenly, add 8.0mmol of 30% KOH aqueous solution dropwise, and stir at room temperature for 2.0-72.0 hours (reaction progress is tracked by TLC); after the reaction, adjust the pH of the reaction solution to strong acidity with 10% hydrochloric acid aqueous solution , then use saturated aqueous sodium bicarbonate solution to adjust the pH of the reaction solution to weak alkalinity, evaporate ethanol under reduced pressure, add 80mL deionized water to the residual liquid, extract three times with 300mL dichloromethane, combine the organic layers with saturated sodium chloride Wash with aqueous solution, dry over anhydrous sodium sulfate, filter, evap...

Embodiment 3

[0068] Example 3 Chalcone Carbamic Acid Esters (I) and Acid Salt Preparation General Method

[0069] In the reaction flask, add the chalcone carbamate 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 Chalcone carbamate compounds ( I ) of the salt, its chemical structure by 1 Confirmed by HNMR and ESI-MS.

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Abstract

The invention discloses a novel carbamate chalcone compound represented by a formula I shown in the description and pharmaceutically acceptable salts thereof, a preparation method for the novel carbamate chalcone compound and the pharmaceutically acceptable salts thereof, a pharmaceutical composition and use of the pharmaceutical composition in the preparation of drugs for treating and / or preventing neurodegenerative related diseases, including, but not limited to neurodegenerative diseases such as vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV related cretinism, multiple sclerosis, progressive lateral spinal sclerosis, neuropathic pain and glaucoma.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a class of novel chalcone carbamate compounds ( I ), its preparation method, pharmaceutical composition and its use in the preparation of drugs for the treatment and / or prevention of 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. 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 Health Organization, 10% of p...

Claims

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Application Information

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IPC IPC(8): C07D295/205C07C271/44C07C269/06A61K31/27A61K31/4453A61K31/495A61K31/40A61K31/5375A61K31/5377A61K31/454A61K31/496A61P25/28A61P25/04A61P27/06A61P25/14A61P25/16A61P25/00
Inventor 邓勇谭正怀强晓明李岩桑志培肖柑媛
Owner SICHUAN UNIV
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