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Chrysin amide derivative and medical application thereof

A pharmacy and compound technology, applied in the field of chrysinamide derivatives and their medicinal uses, can solve the problems that the research of chrysinamide derivatives has not yet been reported, and achieve the effects of excellent antitumor drugs, inhibition of sarcoma size, and easy availability of raw materials

Active Publication Date: 2013-04-24
SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a lot of research has been done on chrysin derivatives in the prior art, research on chrysinamide derivatives has not been reported

Method used

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  • Chrysin amide derivative and medical application thereof
  • Chrysin amide derivative and medical application thereof
  • Chrysin amide derivative and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] N-(1-ethylpyrrolidine-2-methyl)-2-(5-hydroxyl-4-oxygen-2-phenyl-4H-benzopyrone-7-oxyl)acetamide preparation (1 ), the preparation of ethyl 2-(5-hydroxy-2-phenyl-4H-benzopyrone-7-oxo)acetate

[0021]

[0022] Chrysin (2.54g; 0.01mol) and anhydrous potassium carbonate (1.66g; 0.011mol) were added to 100ml of stirred acetone, then ethyl bromoacetate (1.84g, 0.011mol) was added to the solution, and the reaction was Heating to reflux was carried out under the condition of heating (50~60° C.) while stirring, and the reaction time was 6 hours. After the reaction was over, it was cooled. The solution was suction-filtered, and the filtrate was concentrated to 40% of the original volume after suction filtration. The filtrate concentrate was washed with petroleum ether, 1 wt% NaOH solution and water in turn, and then vacuum-dried. The product is a light yellow solid, the product yield is 91%, mp: 242-244°C, 1 H NMR (400MHz, d 6 -DMSO):1.25(t,J=6.9Hz,3H);4.19(m,2H);4.96(S,2H...

Embodiment 2

[0030] 5-Hydroxy-7-(2-oxo-2-piperazinylethoxy)-2-phenyl-4H-benzopyrone

[0031]

[0032] A mixture of dicyclohexylcarbodiimide (DCC, 0.75g; 3.372mmol) and 20ml of anhydrous dichloromethane was dripped into 40ml of anhydrous dichloromethane obtained in step (2) of Example 1 (0.96g; 3.06mmol). In the methyl chloride solution, the whole process was carried out in an ice bath, and after the dropwise addition was completed, the reaction was carried out in an ice bath for 12 hours. Remove the ice bath, add the compound piperazine 3.373mmol and triethylamine TEA (0.341g; 3.372mmol), stir at room temperature for 12 hours, filter with suction, concentrate the filtrate to dryness, then add 80ml of ethyl acetate, and filter with suction , the filtrate was washed 3 times with dilute potassium carbonate solution (concentration 1wt%) and saturated NaCl solution respectively, and the organic phase was washed 3 times with dilute HCl (0.30~0.40wt%), and the aqueous phase was combined, and t...

Embodiment 3

[0034] 2-(5-Hydroxy-4-oxo-2-phenyl-4H-benzopyrone-7-oxyl)-N-(2-piperidinylethyl)acetamide

[0035]

[0036] A mixture of dicyclohexylcarbodiimide (DCC, 0.75g; 3.372mmol) and 20ml of anhydrous dichloromethane was dripped into 40ml of anhydrous dichloromethane obtained in step (2) of Example 1 (0.96g; 3.06mmol). In the methyl chloride solution, the whole process was carried out in an ice bath, and after the dropwise addition was completed, the reaction was carried out in an ice bath for 12 hours. Remove the ice bath, add compound 1-(2-aminoethyl)piperidine 3.373mmol and triethylamine TEA (0.341g; 3.372mmol), stir at room temperature for 12 hours, filter with suction, and concentrate the filtrate to dryness. Then add 100ml of ethyl acetate, filter with suction, wash the filtrate with dilute potassium carbonate solution (concentration 1wt%) and saturated NaCl solution 3 times respectively, wash the organic phase with dilute HCl (0.30~0.40wt%) 3 times, and combine the water phas...

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Abstract

The invention relates to the technical field of medicinal chemistry, and particularly relates to a chrysin amide derivative type compound as well as a preparation method and medical application thereof. The structural formula of the compound provided by the invention is represented by the formula III, wherein a substituent R in the compound is 2-(aminomethyl)-1-ethylpyrrolidine, piperazine, 1-(2-diethyl aminoethyl) piperidine, N, N-dimethylethylenediamine, N, N-diethyl ethylenediamine or 4-piperidinopiperidine. Those compounds can be applied to the preparation of anticancer medicaments.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to lysinamide derivatives and their medical application. Background technique [0002] Chrysin is a flavonoid active compound. Pharmacological studies have shown that chrysin has good antitumor activity, but its pharmacological activity is low due to its own structure and water solubility. At present, the structural modification of chrysin is a research hotspot. Zou Xiaoqing et al. found that acetylated, halogenated, and trifluoromethylated derivatives of chrysin have effects on human gastric cancer (SGC-7901) cells cultured in vitro, human acute myeloid leukemia (HL- 60) cells and human colon cancer (HT-29) cells have inhibitory effect on proliferation, and 6,8-bis-trifluoromethyl-5-hydroxy-7-acetyl chrysin has the strongest effect (Zou Xiaoqing et al. Chinese Pharmacology Bulletin of Science, 2004; 20(4): 453-457). Studies by Li Jiaoling and others have shown that 5-allyl-7-di...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D311/30A61K31/496A61K31/4545A61K31/352A61K31/453A61K31/4025A61P35/00
Inventor 邓旭坤陈旅翼周泽阳
Owner SOUTH CENTRAL UNIVERSITY FOR NATIONALITIES
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