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4-Substituting anilino-3-nitroquinoline compounds, prepn. method and use thereof

A technology of nitroquinoline and anilino, applied in the field of preparation of such compounds, can solve the problems of unknown toxicity of 4-anilinoquinazoline compounds, and achieve the effects of easy preparation and simple structure

Inactive Publication Date: 2006-09-13
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] There are still many problems in the development of EGFR inhibitors, such as the unknown toxicity of 4-anilinoquinazoline compounds that have attracted people's attention, the problem of enzyme selectivity, etc.

Method used

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  • 4-Substituting anilino-3-nitroquinoline compounds, prepn. method and use thereof
  • 4-Substituting anilino-3-nitroquinoline compounds, prepn. method and use thereof
  • 4-Substituting anilino-3-nitroquinoline compounds, prepn. method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Preparation of 6-benzyloxy-7-methoxy-4-(3-ethynylanilino)-3-nitroquinoline (F-1)

[0039] Dissolve isovanillin (9g, 0.059mol) in 40ml of ethanol, add 8.1g of anhydrous sodium carbonate, add distilled benzyl chloride (11.4g, 0.09mol) dropwise, heat to reflux for 5 hours, and spot the plate until the reaction completely. The reaction solution was filtered while it was hot, and the filtrate was evaporated to dryness to obtain an oil, which was solidified at room temperature and recrystallized with ethanol to obtain 10.3 g of 4-benzyloxy-3-methoxybenzaldehyde as a white solid, with a yield of 76%. . h 1 NMR (CDCl 3 ): 9.8 (s, 1H, CHO), 7.3-7.5 (m, 5H, Ph-H), 7.25-7.28 (m, 2H, Ph-H), 7.0 (s, 1H, Ph-H), 5.25 ( s, 2H, PhCH 2 O), 4.0(s, 3H, CH 3 O).

[0040] In an ice bath at 0°C, 4-benzyloxy-3-methoxybenzaldehyde (10 g, 0.041 mol) was slowly added to 40 ml of concentrated nitric acid, and stirring was continued at 15°C for 40 min after the addition was complet...

Embodiment 2

[0048] Example 2 Preparation of 6-benzyloxy-7-methoxy-4-(3-chloroanilino)-3-nitroquinoline (F-2)

[0049] 6-Benzyloxy-7-methoxy-4-chloro-3-nitroquinoline (1.0 g, 2.9 mmol) and 3-chloroaniline (368 mg, 2.9 mmol) were heated in DMF (20 ml) to 100 ℃. After stirring for 24 hours, the solvent was evaporated under reduced pressure, and the residue was recrystallized from methanol to obtain 1.14 g of 6-benzyloxy-7-methoxy-4-(3-chlorophenylamino)-3-nitroquine as a yellow solid Phenyl (F-2), the yield is 90%. h 1 NMR (DMSO): 9.89 (s, 1H, quinoline-2-H), 7.19-7.68 (m, 9H, Ph-H), 5.20 (s, 2H, CH 2 Ph), 4.0(s, 3H, OCH 3 ).

Embodiment 3

[0050] Example 3 Preparation of 6-benzyloxy-7-methoxy-4-(3-bromoanilino)-3-nitroquinoline (F-3)

[0051] 6-Benzyloxy-7-methoxy-4-chloro-3-nitroquinoline (1.0g, 2.9mmol) and 3-bromoaniline (500mg, 2.9mmol) in DMF (20ml) were heated to 100 ℃. After stirring for 24 hours, the solvent was evaporated under reduced pressure, and the residue was recrystallized from methanol to obtain 1.26 g of 6-benzyloxy-7-methoxy-4-(3-bromophenylamino)-3-nitroquine as a yellow solid Phenyl (F-3), yield 91%. h 1 NMR (DMSO): 9.77 (s, 1H, quinoline-2-H), 7.19-7.68 (m, 4H, Ph-H), 5.20 (s, 2H, CH 2 Ph), 4.0(s, 3H, OCH 3 ).

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Abstract

A 4-substituted phenylmino-3-nitroquinoline compound has the suppression action to the reproduction of tumor cells rich in epidermal growth factor receptor. Its preparing process and usage are also disclosed.

Description

technical field [0001] The invention relates to a class of 4-substituted anilino-3-nitroquinoline compounds, which have inhibitory effect on the growth of cells rich in epidermal growth factor receptor (EGFR), and can be used to prepare overtreated or abnormal cells The medicine for the disease caused by proliferation, and the invention also relates to the preparation method of this kind of compound. Background technique [0002] Cancer is a chronic disease that seriously endangers human health. There are 9 million people suffering from cancer in the world every year, and 6 million patients who die from cancer. In my country, the annual incidence of cancer is about 1.2 million, and the number of people who die from cancer every year is as high as 900,000, and more than 1.5 million patients are waiting for treatment. Overcoming the difficulty of cancer is a major task for medical workers. [0003] The drugs that have been studied and applied by people for a long time regard...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/42A61K31/4706A61P35/00
Inventor 罗小民柳红蒋华良李海泓沈旭杜毅丁健林莉萍陈凯先
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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