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A kind of biphenylurea compound containing quinazolinone and its preparation method and application

A technology of quinazolinone and biphenylurea, applied in the field of biomedicine, can solve problems such as hair loss, chemical drugs cannot achieve therapeutic effect, etc., and achieve the effects of inhibiting proliferation and migration, inhibiting growth and migration, and cheap reagents

Inactive Publication Date: 2019-03-01
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 biphenylurea compound containing quinazolinone and its preparation method and application
  • A kind of biphenylurea compound containing quinazolinone and its preparation method and application
  • A kind of biphenylurea compound containing quinazolinone and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] In the structural formula of the biphenylurea compound containing quinazolinone, R 1 is hydrogen, R 2 for CF 3 , prepared by the following steps (see figure 1 ):

[0034] 1) Preparation of compound 1-(3 trifluoromethyl)phenyl)-3-(4-(4,4 ,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (compound 3)

[0035] 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 1.1 g (6.85. Fluoromethylaniline (compound 2) dichloromethane solution, after the dropwise addition, stir for 15min, continue to drop 1.1mL (8.22mmol) triethylamine in dichloromethane solution 10mL into the cloudy solution, and continue stirring for 15min after the dropwise addition , then in the reaction solution, dropwise add 1.50g (6.85mmol) 4-aminophenylboronic acid pinacol ester (compound 1) and 1.1mL (8.22mmol) triethylamine dichloromethane solution 10mL, continue to stir after dropwi...

Embodiment 2

[0046] R in the biphenylurea compound containing quinazolinone 1 , R 2 Both are fluorine.

[0047] Steps 1-2 are the same as Steps 1-2 in Example 1, that is, compound 1-( 3,4-difluoro)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea ( Compound 3). Simultaneously, 7-bromoquinazolin-4(3H)-one (compound 5) was prepared by cyclization reaction between 2-amino-4-bromobenzoic acid (compound 4) and formamide.

[0048] Step 3: 1-(3,4-Difluoro)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl ) phenyl)urea (compound 3) and compound 7-bromoquinazolin-4(3H)-one (compound 5) were prepared by Suzuki coupling reaction to prepare 1-(4-(4-oxo-3,4-di Hydroquinazolin-7-yl)phenyl)-3-(3,4-difluoro)phenyl)urea (Compound 6). The specific operation steps are:

[0049] 1-(3,4-difluoro)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene Base) urea (compound 3) 1.40g (3.74mmol), 7-bromoquinazolin-4 (3H)-one (compound 5) 0.84g (3.74mmol), potassium carb...

Embodiment 3

[0056] R in the biphenylurea compound containing quinazolinone 1 for hydrogen, R 2 for OCF 3 .

[0057] Steps 1-2 are the same as steps 1-2 in Example 1, that is, compound 1-(compound 1-( 4-trifluoromethoxy)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (Compound 3). Simultaneously, 7-bromoquinazolin-4(3H)-one (compound 5) was prepared by cyclization reaction between 2-amino-4-bromobenzoic acid (compound 4) and formamide.

[0058] Step 3: 1-(4-Trifluoromethoxy)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2- 1-(4-(4-oxo-3,4- Dihydroquinazolin-7-yl)phenyl)-3-(4-trifluoromethoxy)phenyl)urea (Compound 6). The specific operation steps are:

[0059] 1-(4-trifluoromethoxy)phenyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) Phenyl) urea (compound 3) 1.40g (3.32mmol), 7-bromoquinazolin-4 (3H)-one (compound 5) 0.82g (3.32mmol), potassium carbonate 1.37g (9.96mmol), four ( Dissolve 0.38 g (0.33 mmol) of triphenylphosphine)palladium in 90 m...

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Abstract

The invention provides a diphenyl urea compound containing quinazolinone and a preparation method and application of the diphenyl urea compound. The structural formula of the compound can be found in description, and R1 and R2 are hydrogen, or isopropyl or a halogen base group. The compound has quite good inhibitory activity to VEGFR-2 kinase, a signal channel induced by the VEGFR-2 kinase can be blocked by inhibiting the activity of the VEGFR-2 kinase, proliferation and migration of tumour cells are inhibited, and thus the diphenyl urea compound can be applied to preparation of antitumor drugs; besides, the preparation method of the compound has the advantages that raw materials are easy to obtain, reaction conditions are mild, the reaction process is easy to operate, and utilized reagent is cheap.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, relates to an anti-tumor compound, in particular to a biphenylurea compound containing quinazolinone 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, et...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88A61P35/00
CPCC07D239/88
Inventor 贺浪冲张杰张彦民潘晓艳代秉玲王金凤苏萍张琳
Owner XI AN JIAOTONG UNIV
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