(1-aryl-1h-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and application thereof

A technology of trimethoxyphenyl and methylphenyl, which is applied in the field of medicine and can solve the problems that the research on anti-tumor activity has not been reported yet.

Inactive Publication Date: 2017-01-04
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The (1-aryl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)methanone and ketone oxime compounds involved in the present invention have not been reported as antitumor activity research

Method used

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  • (1-aryl-1h-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and application thereof
  • (1-aryl-1h-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and application thereof
  • (1-aryl-1h-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0181] Embodiment 1: Preparation of 3-anilino-2-(3,4,5-trimethoxybenzoyl)acrylonitrile

[0182] 3,4,5-trimethoxybenzaldehyde (10.0g, 50.97mmol), potassium hydroxide (8.56g, 152.91mmol), anhydrous copper chloride (0.087g, 0.51mmol), anhydrous acetonitrile (20.92g ,509.68mmol), mixed with 50mL of anhydrous N,N'-dimethylacetamide, and reacted for 12 hours under an oxygen atmosphere. 5. Precipitate a pale yellow solid, filter and dry to obtain the compound 3-oxo-3-(3,4,5-trimethoxyphenyl)propionitrile, which is directly used in the next step without purification. The compound 3-oxo-3-(3,4,5-trimethoxyphenyl)propionitrile (5.0g, 21.25mmol), N,N'-diphenylformamidine (4.17g, 21.25mmol) was added In the reaction bottle, add xylene to dissolve, and reflux reaction under nitrogen protection condition for 2 hours. The xylene was distilled off under reduced pressure, and the compound 3-phenylamino-2-(3,4,5-trimethoxybenzoyl)acrylonitrile could be obtained through separation and purifica...

Embodiment 2

[0183] Example 2: Preparation of (5-amino-1-phenyl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (compound 1)

[0184] Add 3-anilino-2-(3,4,5-trimethoxybenzoyl)acrylonitrile (1.0g, 2.96mmol) and phenylhydrazine hydrochloride (0.43g, 2.96mmol) into the microwave reaction tube, Add an appropriate amount of ethanol to dissolve, add triethylamine (0.30g, 2.96mmol), and react in microwave at 120°C for 20 minutes. After the reaction is completed, the ethanol is evaporated under reduced pressure, and compound 1 can be obtained by separation and purification by column chromatography. Yield 86%. 1 H NMR (400MHz, CDCl 3 ): δ3.93(9H,s),6.09(2H,s),7.09(2H,s),7.44(1H,m),7.55(4H,m),7.85(1H,s)ppm; MS(ESI ):[M+H] + =354.1, [M+Na] + = 376.1.

Embodiment 3

[0185] Example 3: Preparation of (1-phenyl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)methanone (compound 2)

[0186] Add compound 1 (0.50g, 1.42mmol) into an eggplant-shaped bottle, dissolve it with an appropriate amount of tetrahydrofuran, add isoamyl nitrite (0.33, 2.84mmol) dropwise, and react at room temperature for 2 hours. Compound 2 can be obtained by separation and purification by column chromatography. Yield 70%. 1 H NMR (400MHz, CDCl 3 ): δ3.92(6H,s),3.94(3H,s),7.17(2H,s),7.38(1H,t,J=7.4Hz),7.50(2H,dd,J=8.2,J=7.6 Hz), 7.75(2H,d,J=7.6Hz), 8.15(1H,s), 8.50(1H,s)ppm; MS(ESI):[M+H] + =339.1, [M+Na] + = 361.1.

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Abstract

The invention belongs to the technical field of medicines and relates to (1-aryl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)ketone and ketoxime compounds and an application thereof and exactly relates to the compounds and an application thereof to antitumor medicines as tumor cell proliferation inhibitors. A structure of the compounds is shown in a general formula I in the specification: the definition of each substituent is shown in the claim and specification.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a (1-aryl-1H-pyrazol-4-yl)(3,4,5-trimethoxyphenyl)methanone, ketone oxime compound and its application. Specifically, it relates to this type of compound and its application as a tumor cell proliferation inhibitor in antitumor drugs. Background technique [0002] Malignant tumor is a serious disease that threatens human health and life, and it is the leading cause of death in China. Searching for and discovering new drugs for the treatment and prevention of tumors is a major issue at present. [0003] 4-Substituted Methoxyphenyl-aryl-thiazole (4-Substituted Methoxybenzoyl-aryl-thiazole, SMART) compounds were discovered by Miller's research group in 2009, and inhibit melanoma and prostate cancer in vitro to nanomolar levels. SMART is a thiazole that acts on the colchicine-binding site of tubulin. Studies have found that it can destroy the cytoskeleton and induce tumor cell apopt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/38C07D231/12A61K31/415A61P35/00
CPCC07D231/38C07D231/12
Inventor 张为革寨民安吴英良王浩然左代英徐静雯包凯关奇
Owner SHENYANG PHARMA UNIVERSITY
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