Quercetin derivative chemically modified by dodecanoyl chloride and synthesis method thereof

A technology of lauryl chloride chemistry and synthesis method, which is applied in the field of quercetin derivatives chemically modified by lauryl chloride and its synthesis, can solve the problems of poor water solubility and low bioavailability of quercetin, and achieve a simple synthesis method Ease of operation, improved bioavailability, and high product yield

Active Publication Date: 2019-08-16
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention aims to solve the problems of poor water solubility and low bioavailability of quercetin in the prior art, and provides a quercetin derivative. The fat solubility of the obtained quercetin derivative is far better than that of quercetin. The bioavailability has been greatly improved, and it can be used for the treatment of cardiovascular and cerebrovascular diseases, anti-cancer and anti-cancer

Method used

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  • Quercetin derivative chemically modified by dodecanoyl chloride and synthesis method thereof
  • Quercetin derivative chemically modified by dodecanoyl chloride and synthesis method thereof
  • Quercetin derivative chemically modified by dodecanoyl chloride and synthesis method thereof

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Embodiment 1

[0032] A synthetic method for quercetin derivatives, the synthetic route is to use quercetin and lauryl chloride to directly react the target compound under the action of a catalyst, and the method specifically includes the following steps:

[0033] S1. Add 10 mL of anhydrous DMSO to a 100 mL three-neck flask, then add 151 mg of quercetin, dissolve 163.5 mg of lauryl chloride in 3 mL of anhydrous DMSO, slowly drop into the reaction solution, add 18.6 mg of potassium iodide and 25 mg of potassium carbonate; Use a diaphragm vacuum pump to evacuate, nitrogen protection throughout the process, ice-water bath to room temperature and light-shielding reaction, the speed is 650rpm / min, and the reaction is 10h;

[0034] S2. After the reaction, add 0.1mol / L HCL, adjust the pH value to 6-7, add 30mL ethyl acetate and 10ml pure water, extract, separate the liquid, and continue to extract the water layer twice with 30mL ethyl acetate;

[0035] S3. After combining the organic layers obtaine...

Embodiment 2

[0038] A synthetic method for quercetin derivatives, the synthetic route is to use quercetin and lauryl chloride to directly react the target compound under the action of a catalyst, and the method specifically includes the following steps:

[0039] S1. Add 10 mL of anhydrous DMF to a 100 mL three-necked flask, then add 151 mg of quercetin, dissolve 272.5 mg of dodecanoyl chloride in 10 mL of anhydrous DMF, add 25 mg of potassium carbonate and 15.18 mg of triethylamine, and vacuumize with a diaphragm vacuum pump. Nitrogen protection throughout the process, ice-water bath to room temperature shading reaction, rotation speed 650rpm / min, reaction 10h;

[0040] S2. After the reaction, add 0.1mol / L HCL, adjust the pH value to 6-7, add 30mL ethyl acetate and 10ml pure water, extract, separate the liquid, and continue to extract the water layer twice with 30mL ethyl acetate;

[0041] S3. After merging the organic layers obtained each time, add anhydrous sodium sulfate to it and let i...

Embodiment 3

[0044] A synthetic method for quercetin derivatives, the synthetic route is to use quercetin and lauryl chloride to directly react the target compound under the action of a catalyst, and the method specifically includes the following steps:

[0045] S1. Add 10 mL of anhydrous THF to a 100 mL three-neck flask, then add 151 mg of quercetin, dissolve 136.25 mg of lauryl chloride in 10 mL of anhydrous THF, slowly drop into the reaction solution, add 25 mg of sodium carbonate and 15.18 mg of triethyl For amine, use a diaphragm vacuum pump to evacuate, nitrogen protection throughout the process, ice-water bath to room temperature and light-shielding reaction, the speed is 650rpm / min, and the reaction is 10h;

[0046] S2. After the reaction, add 0.1mol / L HCL, adjust the pH value to 6-7, add 30mL ethyl acetate and 10ml pure water, extract, separate the liquid, and continue to extract the water layer twice with 30mL ethyl acetate;

[0047] S3. After combining the organic layers obtaine...

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Abstract

The invention discloses a quercetin derivative chemically modified by dodecanoyl chloride and a synthesis method thereof, belonging to the field of pharmaceutical synthesis. The method comprises the following steps of: adding raw materials namely quercetin and dodecanoyl chloride into a solvent, adding a proper amount of catalyst and acidity regulator, reacting for 8-10 hours under the condition of ice water bath to room temperature, adjusting the pH value to 6-7 with acid after the reaction is finished, adding water, extracting with ethyl acetate, separating liquid, and continuously extracting a water layer with ethyl acetate for 2-3 times. Combine ethyl acetate layers, adde water absorbing agent, overnight, suction filtering, distil to remove ethyl acetate to obtain crude product, purifying with 200-300 mesh silica gel column chromatography, preparing liquid phase, and purifying again to obtain quercetin derivative with high purity. The quercetin derivative obtained by the inventioncarries out chemical modification on natural quercetin, and is favorable for improving water solubility and fat solubility and improving bioavailability through substitution reaction at the 4'-OH hydroxyl position. The quercetin derivative can be used for treating diseases such as hypertension, myocardial ischemia and cancer.

Description

technical field [0001] The invention relates to a method for synthesizing drug derivatives for treating diseases such as hypertension, myocardial ischemia and cancer, in particular to a method for synthesizing quercetin derivatives chemically modified by lauryl chloride. Background technique [0002] Quercetin is a flavonoid compound widely distributed in nature, and exists in large quantities in common plants and vegetables and fruits, such as berries, tea, apples, onions, etc. Quercetin not only has a unique role in cardiovascular disease, cancer prevention and anti-cancer, but also can improve the tumor microenvironment, including reducing the multidrug resistance of tumor cells and competitively inhibiting related metabolic enzymes. Therefore, it has become a research focus of domestic and foreign scholars. [0003] Quercetin (Quercetin), also known as quercetin, quercetin yellow, chemically named 3,5,7,3',4'-pentahydroxyflavone, has a wide range of pharmacological and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P9/10A61P9/12A61P35/00
CPCA61P9/10A61P9/12A61P35/00C07D311/30
Inventor 杨根生金陈浩郭钫元马玉花
Owner ZHEJIANG UNIV OF TECH
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