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Quercetin derivative and preparation method thereof

A technology of quercetin and its derivatives, which is applied in the field of quercetin derivatives and their preparation, can solve the problems of poor water solubility and low bioavailability of quercetin, achieve simple synthesis methods, improve bioavailability, The effect of broad application prospects

Active Publication Date: 2019-08-02
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 and preparation method thereof
  • Quercetin derivative and preparation method thereof
  • Quercetin derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] A kind of preparation method of quercetin derivative comprises the steps:

[0035] Step 1: Preparation of Compound A

[0036] Add 20 mL of DMF to a 100 mL three-neck flask, then add 604 mg of quercetin, add 1308 mg of potassium carbonate and 550 μL of benzyl chloride to the reaction solution, protect the whole process with nitrogen, stir at room temperature for 8 hours, add 30 mL of ethyl acetate and 10 mL of pure water, extraction, liquid separation, and the aqueous layer was extracted twice with 30mL ethyl acetate, and the organic layer obtained from the combined extraction was suction filtered, spin-dried, and purified by 200-300 mesh silica gel column chromatography to obtain compound A, namely 3,7- Bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4H-pyran-4-one;

[0037] Step 2: Preparation of Compound B

[0038] Dissolve 500 mg of compound A in 20 mL of DMF, add 600 μL of lauryl chloride and 300 mg of sodium carbonate to the reaction solution, cover the who...

Embodiment 2

[0042] A kind of preparation method of quercetin derivative comprises the steps:

[0043] Step 1: Preparation of Compound A

[0044] Add 20 mL of DMF to a 100 mL three-neck flask, then add 604 mg of quercetin, add 986 mg of potassium carbonate and 550 μL of benzyl chloride to the reaction solution, protect the whole process with nitrogen, stir at room temperature for 10 hours, add 30 mL of ethyl acetate and 10 mL of pure water, extraction, liquid separation, and the aqueous layer was extracted twice with 30mL ethyl acetate, and the organic layer obtained from the combined extraction was suction filtered, spin-dried, and purified by 200-300 mesh silica gel column chromatography to obtain compound A, namely 3,7- Bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4H-pyran-4-one;

[0045] Step 2: Preparation of Compound B

[0046] Dissolve 500 mg of compound A in 20 mL of DMF, add 600 μL of lauryl chloride and 300 mg of sodium carbonate to the reaction solution, cover the who...

Embodiment 3

[0050] A kind of preparation method of quercetin derivative comprises the steps:

[0051] Step 1: Preparation of Compound A

[0052] Add 20mL THF to a 100mL three-necked flask, then add 604mg of quercetin, add 580mg of DMAP and 550μL of benzyl chloride to the reaction solution, protect the whole process with nitrogen, stir at room temperature for 10 hours, add 30mL of ethyl acetate and 10ml of purified water, Extraction, liquid separation, the aqueous layer continued to be extracted twice with 30mL ethyl acetate, and the organic layers obtained from the combined extraction were suction filtered, spin-dried, and purified by 200-300 mesh silica gel column chromatography to obtain compound A, namely 3,7-bis( Benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-5-hydroxy-4H-pyran-4-one;

[0053] Step 2: Preparation of Compound B

[0054] 500 mg of Compound A was dissolved in 20 mL of THF, 600 μL of lauryl chloride and 300 mg of DMAP were added to the reaction solution, under nitrogen protect...

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Abstract

The invention discloses a quercetin derivative and a preparation method thereof and belongs to the field of medicine synthesis. In order to solve the problems that quercetin is poor in water solubility, low in bioavailability and the like in the prior art, the quercetin derivative is provided, and the obtained quercetin derivative has the lipid solubility far better than quercetin, has greatly improved bioavailability and can be used for treating cardiovascular and cerebrovascular diseases and resisting and preventing cancer. The invention also aims to provide a method for synthesizing the quercetin derivative. The quercetin is used for protecting hydroxyl, a substitution reaction and a hydrogeneration reaction are performed for preparation of the quercetin derivative, and the high-purityquercetin derivative is prepared. The natural quercetin is chemically modified and subjected to a substitution reaction at a 5-OH hydroxyl site, thereby improving the water solubility and lipid solubility of the quercetin and improving the bioavailability. The method adopts a simple principle, the product yield is high and is 37%-57%, the purity reaches 96%-98%, and Rf ranges from 0.2 to 0.5.

Description

technical field [0001] The invention belongs to the field of pharmaceutical synthesis, and relates to a synthesis method of a prodrug for treating diseases such as hypertension, myocardial ischemia and cancer, in particular to a quercetin derivative and a preparation method thereof. Background technique [0002] Many of quercetin and its derivatives are natural products, which generally exist in plants in the form of glycosides. Quercetin and its glycosides have a wide range of pharmacological and physiological activities. Especially in recent years, studies have found that quercetin has anti-arrhythmia, anti-platelet aggregation, anti-oxidation and scavenging oxygen free radicals, treatment of cardiovascular and cerebrovascular diseases, anti-cancer and It has unique effects in anti-cancer and other aspects, and also has anti-virus effects, which has attracted the attention of scholars at home and abroad. [0003] Quercetin (Quercetin), also known as quercetin, quercetin y...

Claims

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Application Information

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IPC IPC(8): C07D311/30A61P9/12A61P9/10A61P35/00
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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