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N-substituted arene aniline / polysubstituted diaryl ether compound, preparation and anti-tumor use thereof

A technology of diaryl ether and aromatic hydrocarbon aniline, which is applied in the field of preparation of anti-tumor drugs, and can solve the problems of unsatisfactory treatment and endangering human life and health

Inactive Publication Date: 2009-04-15
INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although there are about 60 anti-tumor drugs commonly used in clinical practice, the treatment of solid tumors, which are the most serious threat to human life and health and account for more than 90% of malignant tumors, has not achieved satisfactory results.

Method used

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  • N-substituted arene aniline / polysubstituted diaryl ether compound, preparation and anti-tumor use thereof
  • N-substituted arene aniline / polysubstituted diaryl ether compound, preparation and anti-tumor use thereof
  • N-substituted arene aniline / polysubstituted diaryl ether compound, preparation and anti-tumor use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] Example 1: N-(m-hydroxyphenyl)-5-chloro-2,4-dinitroaniline (A1)

[0091] Dissolve 1,5-dichloro-2,4-dinitrobenzene (237mg 1.0mmol) and m-aminophenol (230mg, 2.11mmol) in DMF (0.5mL) and place it directly in an oil bath at 120°C, stirring for 2 Minutes, the reaction solution turned red and cooled to room temperature, adding ice water and dilute HCl to adjust the pH to 3. The solid was filtered out, and the crude product was separated with a silica gel plate, developing solvent: petroleum ether / ethyl acetate, to obtain 208 mg of the title compound as a red solid, with a yield of 67%. 1 H NMR (DMSO) δppm 6.77 (1H, s, ArH-2'), 6.78 (1H, d, J=8.4Hz, ArH-4'), 6.81 (1H, t, J=8.4Hz, ArH-5' ), 7.04 (1H, s, ArH-6), 7.31 (1H, d, J=8.4Hz, ArH-6'), 8.90 (1H, s, ArH-3), 9.83 (1H, s, OH), 10.04 (1H, s, NH).

Embodiment 2

[0092] Example 2: 5-chloro-N-(4'-cyanophenyl)-2,4-dinitroaniline (A2)

[0093] 2,4-Dichloro-1,5-dinitrobenzene (1.2 g, 5 mmol) and p-aniline (0.59 g, 5 mmol) were dissolved in N,N-dimethylformamide (DMF, 10 mL). Potassium tert-butoxide (1.4 g, 12.5 mmol) was added in batches in an ice-water bath, followed by stirring at room temperature for 45 minutes. The reaction solution was poured into ice water, and the pH was adjusted to neutral with dilute HCl. The precipitated solid was filtered off, washed with water, and dried. The crude product was separated on a silica gel column (ethyl acetate / petroleum ether) to obtain the title compound (1.44 g, 90%) as a pale yellow solid. 1 H NMR (CDCl 3 )δppm, 7.41 (1H, s, ArH-6), 7.57 (2H, d, J=8.8Hz, ArH-3', 5'), 7.91 (2H, d, J=8.8Hz, ArH-2', 6'), 8.90 (1H, s, ArH-3), 10.07 (1H, s, NH).

Embodiment 3

[0094] Example 3: 5-chloro-2,4-dinitro-N-(4'-methoxyphenyl)-aniline (A3)

[0095] Dissolve 2,4-dichloro-1,5-dinitrobenzene (0.5 g, 2.11 mmol) and p-methoxyaniline (0.26 g, 2.11 mmol) in DMSO (5 mL), add K 2 CO 3(0.58g, 4.22mmol) and a catalytic amount of metallic Cu were stirred at 115°C for 2 hours under nitrogen protection. Pour into ice water, filter out the solid, wash with water several times, dry the crude product and separate it with a silica gel column (eluted with petroleum ether / ethyl acetate) to obtain the title compound as a reddish-brown solid, 0.68g, yield 67%. 1 H NMR (CDCl 3 )δppm 3.88 (3H, s, OCH 3 ), 7.02 (1H, s, ArH-6), 7.03 (2H, d, J=8.96Hz, ArH-3', 5'), 7.21 (2H, d, J=8.96Hz, ArH-2', 6 '), 9.07 (1H, s, ArH-3), 9.73 (1H, s, NH).

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Abstract

The invention relates to formula (I) N-substituted aromatic hydrocarbon phenyl amines and polysubstitution diaryl ether compounds or medicinal salt thereof, wherein, definitions of X, Y, Z, R1-R4 are shown in a claim, and also relates to a preparing method thereof, a drug combination containing the compounds and the application to anti cancer drug preparation thereof.

Description

Technical field: [0001] The present invention relates to N-substituted aromatic hydrocarbon aniline / multi-substituted diaryl ether compounds or their pharmaceutically acceptable salts with multiple anticancer activities, their preparation method, pharmaceutical composition containing the compound and their use in the preparation of antitumor drugs in the application. Background technique: [0002] Malignant tumors are common and frequently-occurring diseases that seriously threaten human health. According to the report of the World Health Organization, among the 5 billion people in the world, there are about 9 million new cases every year, and 7 million deaths due to tumors, and there is an increasing trend every year. Among the three major therapies for malignant tumors (surgery, chemotherapy, and radiotherapy), drug therapy plays an important role. In recent years, with the development of molecular biology and people's further understanding of the molecular mechanism of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/56C07C209/68C07C255/58C07C253/30C07D213/74A61K31/44A61K31/275A61K31/135A61P35/00
CPCC07C211/56A61P35/00
Inventor 谢蓝秦柄杰田兴涛李国雄
Owner INST OF PHARMACOLOGY & TOXICOLOGY ACAD OF MILITARY MEDICAL SCI P L A
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