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A kind of bisaryl urea compound with antitumor activity and its preparation method and application

An anti-tumor activity, bisaryl urea technology, applied in the field of biomedicine, can solve problems such as hair loss, chemical drugs can not achieve therapeutic effects, etc., to achieve the effect of inhibiting proliferation and migration, inhibiting growth and migration, and inhibiting activity

Inactive Publication Date: 2020-03-17
榆林市第一医院
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, antineoplastic drugs also have many adverse reactions, such as hair loss, vomiting, myelosuppression, rapid drug resistance, etc., which lead to the inability of chemical drugs to achieve the expected therapeutic effect

Method used

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  • A kind of bisaryl urea compound with antitumor activity and its preparation method and application
  • A kind of bisaryl urea compound with antitumor activity and its preparation method and application
  • A kind of bisaryl urea compound with antitumor activity and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] In the structural formula of the bisaryl urea compound with antitumor activity, R 1 for Cl, R 2 for CF 3 , prepared by the following steps (see figure 1 ):

[0032] 1) Compound 1-(4-chloro-3-trifluoromethyl)phenyl)-3-( 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (compound 2)

[0033] Under ice-bath conditions, dissolve 0.80 g (2.74 mmol) of bis(trichloromethyl) carbonate (BTC) with 20 mL of redistilled dichloromethane and stir for 5 min, then slowly add 1.10 g (6.85. mmol) of 4- Chloro-3-trifluoromethylaniline dichloromethane solution, after the dropwise addition, stir for 15min, continue to drop 1.1mL (8.22mmol) triethylamine solution in dichloromethane 10mL to the cloudy solution, continue to Stir for 15min, then add dropwise 1.50g (6.85mmol) 4-aminophenylboronic acid pinacol ester (compound 1) and 1.1mL (8.22mmol) triethylamine in dichloromethane solution 10mL in the reaction solution, after the dropwise addition Stirring was continued for 20 min...

Embodiment 2

[0044] In the structural formula of the bisaryl urea compound with antitumor activity, R 1 for hydrogen, R 2 for chlorine.

[0045] Steps 1) to 2) are the same as steps 1) to 2) in Example 1, that is, compound 1-(3-chlorobenzene is prepared from the starting compound 4-aminophenylboronic acid pinacol ester (compound 1) and m-chloroaniline base)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (compound 2), and then with 2- Amino-6-bromopyridine (compound 3) was prepared by Suzuki coupling to l-(4-(6-aminopyridin-3-yl)phenyl)-2-(3-chlorophenyl)urea (compound 4).

[0046] 3) 1-(4-(6-aminopyridin-3-yl)phenyl)-2-(3-(trichlorophenyl)urea (compound 4) and acryloyl chloride to prepare the target compound through acylation reaction, specifically The operation steps are:

[0047] Under ice bath conditions, 0.28 g (0.83 mmol) of 1-(4-(6-aminopyridin-3-yl) phenyl)-2-(3-(trichlorophenyl) urea (compound 4) was dissolved in In 20mL of anhydrous tetrahydrofuran, slowly add ...

Embodiment 3

[0054] In the structural formula of the bisaryl urea compound with antitumor activity, R 1 for hydrogen, R 2 For fluorine.

[0055] Steps 1) to 2) are the same as steps 1) to 2) in Example 1, that is, compound 1-(2-fluorobenzene is prepared from the starting compound 4-aminophenylboronic acid pinacol ester (compound 1) and o-fluoroaniline base)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (compound 2), and then with 2- Amino-6-bromopyridine (compound 3) was prepared by Suzuki coupling to l-(4-(6-aminopyridin-3-yl)phenyl)-2-(2-fluorophenyl)urea (compound 4).

[0056] 3) 1-(4-(6-aminopyridin-3-yl)phenyl)-2-(2-fluorophenyl)urea (compound 4) and acryloyl chloride to prepare the target compound through acylation reaction, specific operation steps for:

[0057] Under ice bath conditions, 0.30 g (0.93 mmol) of 1-(4-(6-aminopyridin-3-yl) phenyl)-2-(2-fluorophenyl) urea (compound 4) was dissolved in 20 mL of Add 0.52mL (3.72mmol) anhydrous triethylamine dropwise s...

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Abstract

The invention provides diaryl urea compounds with anti-tumor activity as well as a preparation method and an application of the diaryl urea compounds. A structural formula of the compounds is shown in the specification, wherein R1 represents hydrogen or halogen groups, and R2 represents alkane groups or halogen groups. The compounds have good inhibition activity for VEGFR-2 (vascular endothelial growth factor-2) kinase, and can block VEGFR-2 kinase induced signaling pathways and inhibit tumor cell proliferation and migration by inhibiting activity of VEGFR-2 kinase, so that the compounds can be applied to preparation of anti-tumor drugs. Besides, the preparation method of the compounds has the advantages that raw materials are easily available, reaction conditions are mild, a reaction process is simple to operate and used reagents are cheap.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and relates to an antitumor compound, in particular to a bisaryl urea compound with antitumor activity and its preparation method and application. Background technique [0002] Malignant tumors, as one of the largest public health problems in the world, have greatly endangered human health and will become the number one killer of human beings in the new century. Malignant tumors are no longer just a serious disease in developed industrial countries, and developing countries are facing a greater burden of disease. Chemotherapy, as one of the important means of treating tumors, has undergone tremendous development and progress in the past three decades, and a large number of clinical antitumor drugs with different mechanisms of action have been obtained. However, antineoplastic drugs also have many adverse reactions, such as hair loss, vomiting, bone marrow suppression, rapid drug resistance, e...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/75A61P35/00
CPCC07D213/75
Inventor 张杰王金凤潘晓艳张琳卢闻李传圣孙莹王嗣岑
Owner 榆林市第一医院
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