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Trifluoromethylated aniline compound and application thereof

A technology for trifluoromethylated aniline and compounds, which is applied in the field of trifluoromethylated aniline compounds, can solve the problems of uncertain action, increased research cost and difficulty, low yield and the like, and achieves mild reaction conditions, trifluoromethylated aniline and the like. Direct and efficient effect of radical modification method

Active Publication Date: 2020-12-25
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, traditional methods for drug modification generally require long steps, strict conditions, and low yields, which increase the cost and difficulty of research, and the effect on specific tumors is uncertain. Therefore, for the exploration of new anti-tumor drugs, In particular, the simple re-modification of existing arylamine antineoplastic drugs has become a new research direction for drug experts.

Method used

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  • Trifluoromethylated aniline compound and application thereof
  • Trifluoromethylated aniline compound and application thereof
  • Trifluoromethylated aniline compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037]

[0038] Add 46.4mg (0.2mmol) of aminoglutethimide to a mixed solvent of 2ml of DMF and water (1ml:1ml), add 126.4mg (0.4mmol) of 1-(trifluoromethyl)-1,2-benzene Iodosyl-3(1H)-one, 13.3mg (0.04mmol) fluorescein, reacted under blue light irradiation at room temperature for 6 hours, after the reaction, extraction operation: 1. Add saturated NaCl aqueous solution and acetic acid to the reaction solution in sequence Ethyl was extracted twice. 2. Add 50 mL of saturated NaCl aqueous solution and 30 mL of ethyl acetate for the first time to perform one extraction. 3. After the first extraction, collect the organic layer, take the aqueous phase layer and add 20 ml of ethyl acetate for the second extraction. After the extraction was completed, the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was removed by rotary evaporation at room temperature to obtain the crude compound. The crude compound was subjected to silica gel column chromatograph...

Embodiment 2

[0040]In addition to changing the mass and moles of 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-one to 63.2 mg (0.2 mmol), the mass and moles of fluorescein to 0.664 mg (0.002mmol), other operation is constant, and operating procedure is with embodiment 1, obtains the compound pure product 12mg shown in formula (Ia), and reaction yield is 20%.

Embodiment 3

[0042] In addition to changing the mass and moles of 1-(trifluoromethyl)-1,2-phenyliodyl-3(1H)-one to 189.6 mg (0.6 mmol), the mass and moles of fluorescein to 33.2 mg (0.1mmol), other operation is constant, and operating procedure is with embodiment 1, obtains the compound pure product 15mg shown in formula (Ia), and reaction yield is 25%.

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PUM

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Abstract

The invention provides a trifluoromethylated aniline compound as shown in a formula (I) and a preparation method and application thereof. According to the method, trifluoromethylation modification iscarried out on compounds such as aminoglutethimide, the operation process is simple, and raw material sources are commercialized and easy to obtain; and after modification, the anti-tumor activity, especially the anti-cervical cancer activity, of the compound (Ia) is remarkably improved, and particularly the anti-tumor activity of the compound (Ia) is improved by one time or above compared with that of aminoglutethimide. Compared with the conventional aniline drug modification method, the trifluoromethylation modification method adopted by the invention is more direct, efficient and rapid.

Description

[0001] (1) Technical field [0002] The invention belongs to the technical field of organic chemistry, and in particular relates to a trifluoromethylated aniline compound and an application thereof. [0003] (2) Background technology [0004] Tumor is a new organism formed by the body under the action of various tumorigenic factors, and the cells of local tissues lose their normal regulation of their growth at the gene level, resulting in abnormal proliferation and differentiation. Tumor has the characteristics of fast growth, easy metastasis, difficult to cure, and high lethality. It is a major disease that seriously threatens the safety of human life. There are many anti-tumor drugs, and aminoglutethimide is one of them. Aminoglutethimide can inhibit the production of estrogen by blocking aromatase, thereby reducing the promotion effect of estrogen on breast cancer and inhibiting tumor growth. Bacteria are both useful and harmful to the environment, humans and animals. Som...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D211/88C07D239/52C07D261/16A61K31/45A61K31/505A61K31/42A61P35/00
CPCA61P35/00C07D211/88C07D239/52C07D261/16
Inventor 朱勍张方方
Owner ZHEJIANG UNIV OF TECH
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