2-aryl-1,3-isoquinoline diketone anti-tumor compound and synthesis method and application thereof

A technology of isoquinolinedione and its synthesis method, which is applied in the field of 2-aryl-1, can solve the problems of drug resistance and low clinical effective rate, and achieve the goal of easy synthesis, novel structure and inhibition of tumor cell proliferation Effect

Inactive Publication Date: 2012-06-20
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These drugs are used in the clinical treatment of tumors, some of which have low clinical efficacy, and some have developed drug resistance.

Method used

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  • 2-aryl-1,3-isoquinoline diketone anti-tumor compound and synthesis method and application thereof
  • 2-aryl-1,3-isoquinoline diketone anti-tumor compound and synthesis method and application thereof
  • 2-aryl-1,3-isoquinoline diketone anti-tumor compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 6,8-dimethoxy-2-phenyl-1,3-isoquinolinedione (1):

[0037] 3,5-dimethoxy homophthalic anhydride (prepared by reference J.Org.Chem.2003,68,5967-5973) 2.42g (10.89mmol), aniline 1.01g (10.89mmol) and glacial acetic acid ( 20 mL) into a 100 mL round-bottomed flask, the mixture was stirred and refluxed for 5 h under nitrogen protection, cooled to room temperature, slowly poured into water, left to stand overnight, and filtered with suction. The crude product was recrystallized from methanol to obtain 1.70 g of the product. Yield 52.6%. mp: 190-192°C.

Embodiment 2

[0039] Preparation of 6,8-onemethoxy-2-(4-methylphenyl)-1,3-isoquinolinedione (2):

[0040] With embodiment 1, difference is: replace aniline with 4-methylaniline. Yield 64.8%. mp: 160-163°C.

Embodiment 3

[0042] Preparation of 6,8-dimethoxy-2-(4-methoxyphenyl)-1,3-isoquinolinedione (3):

[0043] With embodiment 1, difference is: replace aniline with 4-methoxyaniline. Yield 84.8%. mp: 211-213°C.

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Abstract

The invention relates to 2-aryl-1,3-isoquinoline diketone anti-tumor compound and a synthesis method and application thereof. The 2-aryl-1,3-isoquinoline diketone anti-tumor compound has the chemical structural formula I and the chemical structural formula II, wherein R represents the hydrogen, the hydroxy or the methoxyl, and Ar is phenyl, one or more of the halogen-atom substituted phenyl, the trifluoromethylphenyl, the 3-acetylenyl phenyl, the 6-benzothiazolyl, the 2-acetylamino pyridine and the like. The 2-aryl-1,3-isoquinoline diketone anti-tumor compound has a novel structure, and the synthesis method of the 2-aryl-1,3-isoquinoline diketone anti-tumor compound is easy to implement. The antiproliferative activity assay shows that most compounds have significant functions of inhibiting the growth of human prostate cancer cells PC3 and human kidney cancer cells 786-0, and the in vivo anti-S180 tumor activity test shows that the activity of the compound 21 is significantly stronger than that of Gefitinib.

Description

technical field [0001] The invention belongs to the field of antitumor drugs, relates to an antitumor compound, in particular to a class of 2-aryl-1,3-isoquinolinedione compounds with antitumor activity, a synthesis method and the preparation of antitumor drugs The use of the preparation. Background technique [0002] Malignant tumors seriously threaten human health. In the past 20 years, the morbidity and mortality of malignant tumors in my country have been increasing. The incidence of cancer is about 2 million per 100,000 people, with more than 2.2 million new cases each year and more than 6 million patients under treatment. [0003] At present, the treatment methods for tumors are still traditional surgery, radiation therapy and drug therapy, but to a large extent, drug therapy is still the main method. Therefore, it is of great significance to research and develop new antitumor drugs. [0004] Antineoplastic drugs can be roughly divided into three categories accordin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/24C07D417/04C07D401/04A61K31/472A61K31/4725A61P35/00
Inventor 张三奇康博瑞惠宏襄丁雯曹永孝吕社民
Owner XI AN JIAOTONG UNIV
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