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Preparation method of 6'-amino derivatives based on luteolin structure and application thereof

A technology of amino derivatives and luteolin, which is applied in the field of preparation of luteolin derivatives, achieves the effects of mild conditions, enhanced drug efficacy, product separation and purification, and easy operation

Active Publication Date: 2017-05-17
HUAIHAI INST OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the structural modification of flavonoids mainly focuses on the chemical modification of their C2, C3, C6, C8, C3' (or C5'), and C4' positions, and the introduction of various functional groups with different functions. , such as halogen, alk(oxy) group, aryl group, pyridyl group, amino group, carboxyl group, sulfonic acid group, phosphoric acid group and other groups, so as to improve its solubility, improve its biological activity and bioavailability, and 6 The introduction of amino group at the ' position has not been reported

Method used

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  • Preparation method of 6'-amino derivatives based on luteolin structure and application thereof
  • Preparation method of 6'-amino derivatives based on luteolin structure and application thereof
  • Preparation method of 6'-amino derivatives based on luteolin structure and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: Preparation of luteolin and fatty amine

[0035] Weigh 0.1430 (0.5 mmol) luteolin, pour it into 50 mL of 95% ethanol, and dissolve it under the action of ultrasonic waves. Weigh 1.0 mL (0.1035 g, 0.69 mmol) of 30% methylamine in ethanol, dissolve it in 10 mL of ethanol, and drop the solution into the ethanol solution of luteolin. Add pH = 9.3 carbonate buffer solution dropwise, and measure the final pH of the reaction mixed solution with precision pH test paper to be 9.2, and the mixed solution quickly turns dark red. A reflux condensing device was set up, and the reaction was carried out at 30°C. At the same time, the progress of the reaction was tracked by TLC (developing agent ethanol: ethyl acetate volume ratio = 1.5:3, adding a small amount of ammonia water), the reaction solution was slowly cooled to room temperature, and then extracted three times with 20 mL / ethyl acetate to obtain a bright yellow extract. liquid; the mother liquor was extracted t...

Embodiment 2

[0041] Weigh 0.1430 g (0.5 mmol) of luteolin, add it into 50 mL of 95% ethanol, and dissolve it under the action of ultrasonic waves. Weigh 0.0683 g (0.5 mmol) of an aqueous solution of 33% dimethylamine and dissolve it in 10 mL of ethanol solution, and drop the solution into the ethanol solution of luteolin. Add pH = 9.3 carbonate buffer solution dropwise, and measure the final pH of the reaction mixed solution with precision pH test paper to be 9.2, and the mixed solution quickly turns dark red. A reflux condensing device was added, and the reaction was carried out at 50°C for 24h. At the same time, the progress of the reaction was tracked by TLC (ethanol: ethyl acetate volume ratio = 1:5), the reaction solution was slowly cooled to room temperature, and then extracted three times with 10 mL / ethyl acetate to obtain a yellow extract (i); The mother liquor was extracted four times with 10 mL / time of n-butanol to obtain a reddish-brown extract (ii) and an extract water raffina...

Embodiment 3

[0047] Weigh 1.00 g (0.0035 mol) of luteolin and add 100 mL of absolute ethanol to obtain a pale yellow luteolin suspension. Weigh 0.29 g (0.0105 mol) of ethylamine, dissolve it in a small amount of ethanol solution, and pour it into the luteolin solution. Then weigh 6.90g of sodium hydroxide, add 100mL of water to prepare a sodium hydroxide solution, slowly add it dropwise to the reaction solution, use precision pH test paper to measure the final pH of the reaction mixture solution to be 9.2, and reflux at 50°C. A small amount of ammonia water was added as a developing solvent with methanol: chloroform volume ratio = 1.5:9.0, and plate spotting was carried out during the experimental reaction to track the reaction progress. After the reaction was completed, the reaction solution was slowly cooled to room temperature, filtered with suction, and the filter residue was collected. The mother liquor was rotary evaporated, filtered, and the filter residue was mixed with the filter...

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Abstract

The invention discloses a preparation method of 6'-amino derivatives based on a luteolin structure and an application thereof. Active groups with amino groups of different types are introduced into 6'-position of luteolin in order to prepare derivatives, luteolin and substances with amino active groups are used as raw materials, and a reaction is carried out in a condition with an ethanol-water mixed solvent and a certain acidity; a thin layer chromatography method is used for detecting and tracking the process; after the reaction finishes, a reaction solution is treated in order to obtain products. Oxidation and Michael addition and the like are reacted continuously in order to synthesize amino luteolin o-quinone derivates which may be stable, and the method has the advantages of a few reaction steps, operation convenience, low toxicity, mild condition, and low cost; non-steroidal anti-inflammatory medicament with the novel structure is prepared, and drug effects are enhanced; lipid / water participation coefficient of the whole molecule is adjusted, and pharmacokinetic parameters of lead compounds are influenced; pharmacological tests are carried out in order to research structure-function relationship of the luteolin compound, and non-steroidal anti-inflammatory medicament with good curative effect and small toxic and side effects are screened.

Description

technical field [0001] The invention discloses a preparation method of a luteolin derivative, in particular a preparation method and application of a 6' amino derivative based on a luteolin structure. Background technique [0002] The chemical name of luteolin is 3',4',5,7-tetrahydroxyflavone (3',4',5,7-Tetralydoxyflanone), and the chemical formula is C 15 h 10 o 6 , with a molecular weight of 286.23, belonging to flavonoids. Luteolin is yellow powder, soluble in organic solvents such as ethanol and ether, slightly soluble in hot water, hardly soluble in cold water. Luteolin has some pharmacological activities: anti-oxidation, antibacterial effect, treatment of chronic bronchitis, anti-tumor effect. In the structure of most clinically used non-steroidal anti-inflammatory drugs, the α, β-unsaturated carbonyl structure makes the drug have anti-inflammatory and anti-cancer activities, and most of its molecular structure features amino groups or derivations, such as thiazide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P29/00
CPCC07D311/30
Inventor 王建刘玮炜王芙蓉张伟周璐杨帆姚东瑞
Owner HUAIHAI INST OF TECH
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