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Application of 7-hydroxycoumarin pyrazoline derivatives in the preparation of drugs for stabilizing arteriosclerotic plaques

A technology of arteriosclerosis and pyrazole, applied in the application field of 7-hydroxycoumarin pyrazoline derivatives in the preparation of drugs for stabilizing arteriosclerotic plaques, to achieve the effects of improving stability, improving plaque structure, and inhibiting apoptosis Effect

Active Publication Date: 2020-04-10
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

After searching by authoritative organizations, the biological activity of 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)-7-hydroxy-2H-chromen-2-one, Especially in the study of stabilizing atherosclerotic plaque, there is no report at home and abroad

Method used

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  • Application of 7-hydroxycoumarin pyrazoline derivatives in the preparation of drugs for stabilizing arteriosclerotic plaques
  • Application of 7-hydroxycoumarin pyrazoline derivatives in the preparation of drugs for stabilizing arteriosclerotic plaques
  • Application of 7-hydroxycoumarin pyrazoline derivatives in the preparation of drugs for stabilizing arteriosclerotic plaques

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Preparation of 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)-7-hydroxy-2H-chromen-2-one

[0047] 2,4-Dihydroxybenzaldehyde (20mmol) and ethyl acetoacetate (24mmol) were dissolved in 30ml of ethanol solution, and 1ml of piperidine was added dropwise as a catalyst. The reaction solution was heated to reflux for 3 hours to the end of the reaction, and a large amount of grass green solid was precipitated after cooling to room temperature. The crude product is obtained by suction filtration, and then recrystallized with ethanol to obtain the green product 7-hydroxy-3-acetyl coumarin.

[0048] Dissolve 7-hydroxy-3-acetylcoumarin, benzaldehyde and a catalytic amount of piperidine (about 1 ml) in 20 ml of absolute ethanol, and reflux the reaction solution for 4 hours to cool to room temperature. Since this reaction has a low conversion rate under weak alkaline conditions, 10 equivalents of benzaldehyde are added for the reaction. The excess benzaldehyde was washed away w...

Embodiment 2

[0050] Example 2: The effect of HCP1 on vascular endothelial cell apoptosis

[0051] After inoculating human umbilical vein endothelial cells in a 24-well cell culture plate and culturing for 24 hours, set the normal group: 10% serum, 2μl / ml growth factor under normal conditions; control group: serum and growth factor starvation conditions The experimental group: cultured with 1μM HCP1 under the condition of removing serum and growth factors. 37°C, CO 2 After 24h and 48h incubation in the incubator, observe and take pictures under an inverted microscope (100X).

[0052] After inoculating human umbilical vein endothelial cells in a 96-well cell culture plate and culturing for 24 hours, set the normal group: 10% serum, 2μl / ml growth factor under normal conditions; control group: serum and growth factor starvation conditions The experimental group: cultured with HCP1 at concentrations of 0.01 μM, 0.1 μM, 0.25 μM, 0.5 μM, 0.75 μM, 1 μM, 2.5 μM, and 5 μM under the condition of removing...

Embodiment 3

[0055] Example 3: The effect of HCP1 on the composition of atherosclerotic plaque

[0056] Take eight-week-old apoE - / - Mice (purchased by Beijing Weitong Lihua Laboratory Animal Technology Co., Ltd.) were fed with high-fat feed (formula: 0.15% cholesterol, 21% fat) until the deadline for obtaining materials. The experimental mice were randomly divided into three groups: the reference group, the control group (dimethyl sulfoxide solvent control), and the HCP1 treatment group (1 mg / kg / day). The benchmark group was dissected after 20 weeks of high-fat feeding, and the other groups continued high-fat feeding and received intraperitoneal injection of drugs for 8 weeks. The specific treatment methods are shown in the attachment Figure 5 . The mice treated with drugs were dislocated and sacrificed, and the aorta was stripped. The aortic root was frozen and embedded and sliced ​​for later use. The aorta was longitudinally sectioned, washed with PBS, and frozen and stored.

[0057] Fro...

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Abstract

The invention discloses an application of a 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazole-3-group)-7-hydroxyl-2H-chromene-2-ketone in the preparation of a drug for stabilizing an arteriosclerosis plaque, wherein the dose of the 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazole-3-group)-7-hydroxyl-2H-chromene-2-ketone for effectively stabilizing the arteriosclerosis plaque is 1 mg / kg / day. The experiment proves that the 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazole-3-group)-7-hydroxyl-2H-chromene-2-ketone has the advantages of being capable of significantly reducing the apoptosis rate of endothelial cells in aortic plaques and the apoptosis rate of cells in aortic root plaques; improving the structure of the plaques; improving the stability of the plaques; being capable of being used as an effective tool for studying an unstable molecular mechanism of the atherosclerosis plaque; laying a groundwork for developing the drug to treat arteriosclerosis.

Description

Technical field [0001] The present invention relates to a pharmaceutical use of a coumarin pyrazoline derivative, in particular to a 7-hydroxycoumarin pyrazoline derivative, namely 3-(1,5-diphenyl-4,5-dihydro-1H) -Pyrazol-3-yl)-7-hydroxy-2H-chromen-2-one in the preparation of drugs for stabilizing arteriosclerosis plaque. Background technique [0002] The structural formula of 3-(1,5-diphenyl-4,5-dihydro-1H-pyrazol-3-yl)-7-hydroxy-2H-chromen-2-one is: [0003] [0004] Molecular formula: C 24 H 18 N 2 O 3 [0005] Molecular weight: 382.1317, properties: solid powder [0006] Coumarin is an important type of natural organic compound in nature with a variety of pharmacological activities. Its mechanism of action is mainly to scavenging oxygen free radicals, blocking lipid peroxidation, inhibiting sodium and calcium plasma channels, and regulating human cytokines , Expression of adhesion molecules, enzymes and other proteins. 4-Schiff base-7-benzyloxycoumarin and its derivatives synth...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/4155A61P9/10
CPCA61K31/4155
Inventor 苗俊英赵宝祥张尚立苏乐魏群
Owner SHANDONG UNIV
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