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Method for synthesizing azophenylene amide compound with antineoplastic activity and application of azophenylene amide compound

A technology of anti-tumor activity and phenazinamide, which is applied in the field of synthesis of phenazine amide compounds, can solve the problems of high toxicity and side effects of anti-tumor drugs, and achieve the effects of safe clinical medication, easy preparation method, and convenient source of raw materials

Active Publication Date: 2016-03-23
高小春
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem of large toxic and side effects of anti-tumor drugs in the prior art, the present invention provides the synthesis and application of a phenazine amide compound with anti-tumor activity that can kill tumor cells and has no toxic and side effects on normal cells

Method used

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  • Method for synthesizing azophenylene amide compound with antineoplastic activity and application of azophenylene amide compound
  • Method for synthesizing azophenylene amide compound with antineoplastic activity and application of azophenylene amide compound
  • Method for synthesizing azophenylene amide compound with antineoplastic activity and application of azophenylene amide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] A kind of synthesis of the phenazine amides compound with antitumor activity, comprises the following steps:

[0037] Add 1.3g of aniline hydrochloride, 1.4g of o-nitroaniline and 4.2g of zinc chloride into the reaction flask, and stir the reaction at 160°C for 10min. After the reaction, cool the reactant to 25°C and pour Adding mass concentration is 25% sodium hydroxide solution 15ml to neutralize the acid generated by the reaction, remove the liquid obtained in the reaction flask by filtration, add 70ml ethanol to the obtained filter residue and reflux, collect the extract, and after reflux for 25min, pour the obtained filter residue Then add 70ml of ethanol to continue to reflux, collect the extract, and after reflux for 25min, add 70ml of ethanol to the obtained filter residue to continue to reflux, collect the extract, combine the three extracts together, remove the liquid in the extract, and get the crude product , mix the crude product with silica gel, pass through...

Embodiment 2

[0040] A kind of synthesis of the phenazine amides compound with antitumor activity, comprises the following steps:

[0041] Add 2g of aniline hydrochloride, 2.1g of o-nitroaniline and 4.5g of zinc chloride into the reaction flask, and stir the reaction at 180°C for 15 minutes. After the reaction, cool the reactant to 27°C, and add Mass concentration is the acid that 18ml of sodium hydroxide solution 18ml of 25% neutralizes reaction to generate, filter and remove the liquid that obtains in the reaction flask, add 75ml ethanol and reflux in the obtained filter residue, collect extract, after reflux 30min, pour into the obtained filter residue Add 75ml of ethanol again and continue to reflux, collect the extract, after reflux for 30min, add 75ml of ethanol again to the resulting filter residue and continue to reflux, collect the extract, combine the three extracts together, remove the liquid in the extract to obtain a crude product, Mix the crude product with silica gel, pass th...

Embodiment 3

[0044] A kind of synthesis of the phenazine amides compound with antitumor activity, comprises the following steps:

[0045] Add 2.6g of aniline hydrochloride, 2.8g of o-nitroaniline and 8.4g of zinc chloride into the reaction flask, and stir the reaction at 200°C for 20min. Adding mass concentration is 25% sodium hydroxide solution 20ml to neutralize the acid generated by the reaction, remove the liquid obtained in the reaction flask by filtration, add 80ml ethanol to the obtained filter residue and reflux, collect the extract, and after reflux for 35min, pour the obtained filter residue Add 80ml of ethanol to continue to reflux, collect the extract, and after reflux for 35min, add 80ml of ethanol to the obtained filter residue to continue to reflux, collect the extract, combine the three extracts together, remove the liquid in the extract, and obtain the crude product , mix the crude product with silica gel, pass through the column, use petroleum ether-ethyl acetate system, ...

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Abstract

The invention relates to a method for synthesizing an azophenylene amide compound with antineoplastic activity and an application of the azophenylene amide compound. The method includes the following steps that aniline hydrochloride and ortho-nitroaniline are reacted under the catalyst condition, processing is carried out after the reaction is finished, and a red solid azophenylene-2-amine is obtained; the azophenylene-2-amine is dissolved into dichloromethane, then triethylamine is added into the reaction liquid, the reaction liquid is stirred to be even and cooled to the temperature lower than 15 DEG C, a chloroacetyl-chloride-dissolving dichloromethane solution is slowly added into the reaction liquid, the mixture is stirred and reacted for 30-60 min under the condition of -15 DEG C, solvents are removed, a crude product is obtained, and a light-yellow solid 2-chlorine-N-(2-azophenylene)acetamide is obtained after the crude product is purified. The method has the advantages that according to the azophenylene amide compound with the antineoplastic activity, clinical medication is safe, the preparing method is simple, raw material sources are convenient, industrialization can be achieved, the requirements of antineoplastic medicine can be met, and the azophenylene amide compound is expected to be developed into new antineoplastic medicine.

Description

technical field [0001] The invention relates to the synthesis of a phenazine amide compound, in particular to the synthesis and application of a phenazine amide compound with antitumor activity. Background technique [0002] Cancer is the first cause of death among residents in our country, and with the development of economy and the pollution of the environment, the mortality rate of cancer is constantly rising, seriously endangering people's lives and people's quality of life. At present, people often treat cancer by means of surgery and chemotherapy, which have caused serious harm to people's spirit and body. At present, the antineoplastic drugs taken by cancer patients not only kill tumor cells, but also kill a large number of normal cells. With toxic side effects. Such as: nausea, mouth ulcers, vomiting, diarrhea, hematuria, decreased immunity, susceptibility to infection, leukopenia, thrombocytopenia, etc., causing great harm to the human body. Therefore, finding an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/46A61P35/00
CPCC07D241/46
Inventor 高小春
Owner 高小春
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