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A cyclosuccinamide compound with antitumor activity and its preparation method and application

A technology of cyclosuccinamide and anti-tumor activity, applied in the field of biomedicine, can solve problems such as hair loss and chemical drugs that cannot achieve therapeutic effects, and achieve the effect of inhibiting proliferation and migration, inhibiting growth and migration, and inhibiting activity

Active Publication Date: 2018-07-17
XI AN JIAOTONG UNIV
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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 cyclosuccinamide compound with antitumor activity and its preparation method and application
  • A cyclosuccinamide compound with antitumor activity and its preparation method and application
  • A cyclosuccinamide compound with antitumor activity and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In the structural formula of the cyclosuccinamide compound with antitumor activity, R 1 for hydrogen, R 2 For F, prepared by the following steps (see figure 1 ):

[0036] 1) Preparation of 7-bromoquinazolin-4(3H)-one (compound 2) by cyclization reaction of 2-amino-4-bromobenzoic acid (compound 1) and formamide

[0037] Dissolve 5.0g (23.14mmol) of 2-amino-4-bromobenzoic acid in 80ml (2.01mmol) of formamide, and react for 1.45h under nitrogen protection at 150°C and a microwave power of 300W. After the reaction, the The reaction solution was added to ice water, extracted 3-4 times with ethyl acetate, and the extracted organic phase was washed with saturated sodium bicarbonate solution and saturated brine successively, then dried with anhydrous sodium sulfate, and then spin-dried to obtain a reddish-brown residue , the reddish-brown residue was separated by chromatography to obtain 1.89 g of reddish-brown solid 7-bromoquinazolin-4(3H)-one with a yield of 36.3%.

[003...

Embodiment 2

[0050] In the structural formula of the cyclosuccinamide compound with antitumor activity, R 1 , R 2 Both are trifluoromethyl.

[0051] Step 1) to step 3) are the same as step 1) to step 3) in Example 1, that is to prepare 7- Bromoquinazolin-4(3H)-one (compound 2), 7-bromoquinazolin-4(3H)-one (compound 2) and p-aminophenyl borate hydrochloride (compound 3) were obtained by Suzuki reaction 4((3H)-7-quinazolin-4-one)aniline (compound 4), 1,1 cyclobutyldicarboxylic acid (compound 5) and 3,5-ditrifluoromethylaniline (compound 6) in The acylation reaction under the condition of thionyl chloride gave 1-((3,5-bistrifluoromethylphenyl)carbamoyl)cyclobutanecarboxylic acid (compound 7).

[0052] 4) 4((3H)-7-quinazolin-4-one)aniline (compound 4) and 1-((3,5-bistrifluoromethylphenyl)carbamoyl)cyclobutyric acid (compound 7 ) generates the target compound (compound 8) under the condensation of HATU condensing agent, and the specific operation steps are:

[0053] Under ice-bath conditio...

Embodiment 3

[0060] In the structural formula of the cyclosuccinamide compound with antitumor activity, R 1 is chlorine, R 2 for CH 3 .

[0061] Step 1) to step 3) are the same as step 1) to step 3) in Example 1, that is to prepare 7- Bromoquinazolin-4(3H)-one (compound 2), 7-bromoquinazolin-4(3H)-one (compound 2) and p-aminophenyl borate hydrochloride (compound 3) were obtained by Suzuki reaction 4((3H)-7-quinazolin-4-one)aniline (compound 4), 1,1 cyclobutyldicarboxylic acid (compound 5) and 3-chloro-4-methylaniline (compound 6) in chlorine Acylation under sulfoxide conditions gave 1-((3-chloro-4-methylphenyl)carbamoyl)cyclobutanecarboxylic acid (compound 7).

[0062] 4) 4((3H)-7-quinazolin-4-one)aniline (compound 4) and 1-((3-chloro-4-methylphenyl)carbamoyl)cyclobutyric acid (compound 7) Generate the target compound (compound 8) under the condensation of HATU condensing agent, and the specific operation steps are:

[0063] Under ice-bath condition, 0.59g (2.49mmol) 4 ((3H)-7-quinaz...

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Abstract

The invention provides a cyclobutane-diamide compound with antitumor activity and a preparation method and application thereof. The structure formula of the compound is shown in the description, wherein R1 and R2 are hydrogen, alkane groups or halogen groups. The compound has very good inhibitory activity for VEGFR-2 kinase and can cut off an inductive signal channel of the VEGFR-2 kinase and restrain hyperplasia and migration of tumor cells by restraining the activity of the VEGFR-2 kinase, and therefore the compound can be applied to preparation of antitumor drugs. The preparation method of the compound has the advantages that raw materials are easy to get, reaction conditions are mild, operation is easy in the reaction process, and adopted reagents are low in price.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and relates to an antitumor compound, in particular to a cyclosuccinamide 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 resistanc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/88A61K31/517A61P35/00
CPCC07D239/88
Inventor 张杰卢闻王金凤潘晓艳张琳贺浪冲王嗣岑张涛
Owner XI AN JIAOTONG UNIV
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