A class of carbamate chalcone ester compounds, their preparation methods and uses

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

Inactive Publication Date: 2017-11-07
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), although these compounds have good acetylcholinesterase inhibitory and antioxidant activity, but for A β 1-42 Inhibition of self-aggregation (inhibition rates of less than 30.0% at 25.0 µM concentration), Cu 2+ Induced A β 1-42 Inhibition of aggregation (inhibition rates of less than 35.0% at a concentration of 25.0 µM) and 2+ Induced A β 1-42 The aggregation disaggregation activity (the disaggregation rate is less than 35.0% at 25.0 µM concentration) is not satisfactory, resulting in the suboptimal efficacy of these compounds against AD in animal models

Method used

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  • A class of carbamate chalcone ester compounds, their preparation methods and uses
  • A class of carbamate chalcone ester compounds, their preparation methods and uses
  • A class of carbamate chalcone ester compounds, their preparation methods and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 General method for the preparation of chalcone carbamate esters (I)

[0048] Add 2.0 mmol of the corresponding 2-hydroxyacetophenone compound (2), 3.0 mmol of the corresponding benzaldehyde compound (1), 8.0 mmol of anhydrous potassium carbonate and 50 ml of acetonitrile into the reaction flask, stir evenly, and heat up to reflux Stir the reaction 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% aqueous hydrochloric acid solution, and then adjust the pH of the reaction solution to weak alkaline with saturated aqueous sodium bicarbonate solution , acetonitrile was evaporated under reduced pressure, 80 mL of deionized water was added to the residual liquid, extracted three times with 300 mL of dichloromethane, the organic layers were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, fi...

Embodiment 2

[0058] Example 2 The General Method for the Preparation of Chalcone Carbamic Acid Esters (I)

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

Embodiment 3

[0068] Example 3 General method for preparation of chalcone carbamate ester compound (I) and acid salt formation

[0069] Add 2.0 mmol of the chalcone carbamate ester compound (I) obtained according to the above-mentioned Example 1 or 2 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 After cooling to room temperature, the solvent was distilled off under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain the salt of chalcone carbamate compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a novel class of chalcone carbamate compounds (I) and pharmaceutically acceptable salts thereof, their preparation methods, pharmaceutical compositions and their use in preparing drugs for the treatment and / or prevention of neurodegenerative related diseases. Uses, 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 neurological diseases Degenerative diseases.

Description

technical field [0001] The present invention belongs to the field of medicinal chemistry, and relates to a new type of chalcone carbamate compound (I), its preparation method, pharmaceutical composition and its use in the preparation of drugs for the treatment and / or prevention of neurodegenerative 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. According to the report o...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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