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Preparation method and application of chalcone derivative QNL-Chalcone

A technology of chalcone derivatives and ethyl ketone, which is applied in drug combinations, nervous system diseases, organic chemistry, etc., can solve the problems of strong antidepressant activity, insufficient molecular activity, and long synthetic route, and achieve low price and easy scale-up. The effect of large-scale industrial mass production and short synthetic route

Active Publication Date: 2020-01-31
ZHEJIANG OCEAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The present invention provides a preparation of a chalcone derivative QNL-Chalcone in order to overcome the problems of insufficient molecular activity and long synthetic routes of the inventions of the prior art The method and application not only introduce the quinoline core, but also retain the chalcone activity essential group - acrylone structure, to the compound QNL-Chalcone with strong antidepressant activity and low side effects

Method used

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  • Preparation method and application of chalcone derivative QNL-Chalcone
  • Preparation method and application of chalcone derivative QNL-Chalcone
  • Preparation method and application of chalcone derivative QNL-Chalcone

Examples

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Embodiment 1

[0036] A preparation method and application of a chalcone derivative QNL-Chalcone, comprising the following steps:

[0037] (1), the synthesis of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone:

[0038]

[0039] (2), the synthesis of QNL-Chalcone:

[0040]

[0041] The specific process of the step (1) is: take 4.8 mmol of acetylacetone and 2.1 mmol of citric acid in a round-bottomed flask, stir and reflux on a magnetic stirrer at a temperature of 102 ° C, and mix 4.3 mmol of 2-amino di Benzophenone was dissolved in 16ml of 1,4-dioxane in a constant-pressure dropping funnel, and slowly dropped into a round-bottomed flask under stirring conditions, and the reaction progress was monitored by TLC. After the reaction, add 2mol KOH solution to the reaction system, extract 3 times with 31ml ethyl acetate, wash with water until neutral, anhydrous Na 2 SO 4 Dry, filter with suction, spin dry, and recrystallize from ethanol to obtain compound 1-(2-methyl-4-phenylquinolin-3-yl)ethan...

Embodiment 2

[0058] The difference from Example 1 is that the specific process of the step (1) is: take 4.8 mmol of acetylacetone and 2 mmol of citric acid in a round-bottomed flask, stir and reflux on a magnetic stirrer at a temperature of 95° C., and 4mmol of 2-aminobenzophenone was dissolved in 15ml of 1,4-dioxane in a constant-pressure dropping funnel, slowly dropped into a round-bottomed flask under stirring conditions, and the reaction progress was monitored by TLC. After the reaction, add 1.9mol KOH solution to the reaction system, extract 3 times with 30ml ethyl acetate, wash with water until neutral, anhydrous Na 2 SO 4 Dry, filter with suction, spin dry, and recrystallize from ethanol to obtain compound 1-(2-methyl-4-phenylquinolin-3-yl)ethanone (1a).

[0059] The specific process of step (2) is: get 2mmol of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone (1a), 2.2mmol of 2-bromobenzaldehyde in a round bottom flask, add 28ml of 4% KOH ethanol solution was stirred at room temperatur...

Embodiment 3

[0061] The difference from Example 1 is that the specific process of the step (1) is: take 4.8 mmol of acetylacetone and 2.2 mmol of citric acid in a round bottom flask, stir and reflux on a magnetic stirrer at a temperature of 110 ° C, Dissolve 4.5 mmol of 2-aminobenzophenone in 18 ml of 1,4-dioxane in a constant-pressure dropping funnel, slowly drop into a round-bottomed flask under stirring, and monitor the reaction progress by TLC. After the reaction, add 2.1mol KOH solution to the reaction system, extract 3 times with 32ml ethyl acetate, wash with water until neutral, anhydrous Na 2 SO 4 Dry, filter with suction, spin dry, and recrystallize from ethanol to obtain compound 1-(2-methyl-4-phenylquinolin-3-yl)ethanone (1a).

[0062] The specific process of step (2) is: get 2mmol of 1-(2-methyl-4-phenylquinolin-3-yl)ethanone (1a), 2.6mmol of 2-bromobenzaldehyde in a round bottom flask, add 32ml of 4.5% KOH ethanol solution was stirred at room temperature, and the reaction pr...

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Abstract

The invention relates to the field of drug synthesis, and discloses a preparation method and application of a novel chalcone derivative QNL-Chalcone aiming at the problems of insufficient molecular activity and long synthesis route in the prior art. The preparation method comprises the following steps: (1) synthesis of 1-(2-methyl-4-phenylquinoline-3-yl) ethanone; and (2) synthesis of QNL-Chalcone; wherein acetylacetonamine, 2-aminobenzophenone and 2-bromobenzaldehyde are taken as raw materials, and QNL-Chalcone is prepared through the above two preparation steps. According to the invention, quinoline parent nucleuses are introduced, and a chalcone activity essential group: acrylketone structure is reserved, so that the compound QNL-Chalcone with strong anti-depression activity and low side effect is obtained; the synthetic route of the medicine is short, the cost is low, the process is good in controllability and easy for actual large-scale industrial mass production, and the preparedproduct is high in yield and purity.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a preparation method and application of a chalcone derivative QNL-Chalcone. Background technique [0002] Depression is a mental disorder characterized by disturbance of emotional activity, characterized by abnormally depressed mood, often with strong suicidal tendencies, and accompanied by autonomic or somatic symptoms. The main clinical manifestations are unhappiness, irritability, sadness, restlessness and depression, indifference and lack of interest in things around, inhibition of thought and action, insomnia and other signs. Depression will have a serious impact on the body's function, and the The disease is characterized by high morbidity, refractory cure and high recurrence rate. Existing antidepressants are not effective in treatment. [0003] Quinoline compounds have a variety of biological activities, and many drugs containing quinoline cores are used clinically. Accor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/14A61P25/24
CPCC07D215/14A61P25/24
Inventor 关丽萍彭鼎新张珊珊何丽雅
Owner ZHEJIANG OCEAN UNIV
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