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Acylhydrazone compounds with anti-tumor activity as well as preparation method and application of acylhydrazone compounds

A technology of anti-tumor drugs and compounds, applied in the preparation of hydrazones, anti-tumor drugs, organic active ingredients, etc., can solve long-term problems and achieve good inhibitory effects

Inactive Publication Date: 2018-03-23
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the research and development of new anti-tumor drugs still needs a long process to achieve a real cure for tumors.

Method used

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  • Acylhydrazone compounds with anti-tumor activity as well as preparation method and application of acylhydrazone compounds
  • Acylhydrazone compounds with anti-tumor activity as well as preparation method and application of acylhydrazone compounds
  • Acylhydrazone compounds with anti-tumor activity as well as preparation method and application of acylhydrazone compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The synthesis of embodiment 1 4-methyl nitrobenzoate

[0024] Take a 25ml single-necked bottle, add 5ml of methanol and 0.4g of M1 in the following formula in sequence, stir, slowly add 1ml of concentrated sulfuric acid dropwise, and reflux at 80°C for 3h. After the reaction was completed, the methanol was spin-dried under reduced pressure, the pH was adjusted to 9 by adding a saturated sodium carbonate solution dropwise, 5ml of dichloromethane was added, the layers were separated, the organic layer was washed 3 times with saturated sodium chloride, the aqueous layer was combined, and dichloromethane extracted two Once, the organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate for 1 hour. The ratio of petroleum ether to ethyl acetate was 5:1 and separated through a silica gel column to obtain M1' with a yield of 95%.

[0025] The overall reaction formula is as follows:

[0026]

Embodiment 2

[0027] Synthesis of Example 2 (1,1'-biphenyl)-4-carboxylic acid methyl ester

[0028] Take a 25ml single-necked bottle, add 5ml of methanol and 0.5g of M2 in the following formula successively, stir, slowly add 1ml of concentrated sulfuric acid dropwise, and reflux at 80°C for 3h. After the reaction, the methanol was spin-dried under reduced pressure, the pH was adjusted to 9 by adding a saturated sodium carbonate solution dropwise, 5ml of dichloromethane was added, the layers were separated, the organic layer was washed 3 times with saturated sodium chloride, the aqueous layer was combined, and dichloromethane extracted two Once, the organic layers were combined, and the organic phase was dried over anhydrous sodium sulfate for 1 hour. The ratio of petroleum ether to ethyl acetate was 5:1 and separated through a silica gel column to obtain M2' with a yield of 96%.

[0029] The overall reaction formula is as follows:

[0030]

Embodiment 3

[0031] Example 3 Synthesis of 4-amino-3-methoxybenzoic acid methyl ester

[0032] Take a 25ml single-necked bottle, add 5ml of methanol and 0.5g of 4-amino-3-methoxybenzoic acid in sequence, stir, slowly add 1ml of concentrated sulfuric acid dropwise, and react under reflux at 80°C for 3h. After the reaction was monitored by TLC, methanol was spin-dried under reduced pressure, and saturated sodium carbonate solution was added dropwise to adjust the pH to 9, and 5ml of dichloromethane was added for liquid separation. Extract twice, combine the organic layers, and dry the organic phase with anhydrous sodium sulfate for 1 hour. The ratio of petroleum ether to ethyl acetate was 4:1 and separated through a silica gel column to obtain 0.52 g of off-white solid methyl 4-amino-3-methoxybenzoate with a yield of 96%.

[0033] The overall reaction formula is as follows:

[0034]

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Abstract

The invention belongs to the technical field of medicinal chemistry, and in particular relates to acylhydrazone compounds with anti-tumor activity as well as a preparation method and application of the acylhydrazone compounds. The structures of the acylhydrazone compounds are as shown in a general formula (I) shown in the description, wherein R and R' are independently selected from any one or more of halogen, amino, cyano, alkoxy, 3,4-methylenedioxy, nitro, phenyl or substituted phenyl, and R and R' substituents are mono-substituted, disubstituted or tri-substituted. The preparation method issimple; biological activity test results of the compounds show that the compounds have a very good inhibitory effect on histone methyltransferase SET7, and have good application prospect in the development of anti-tumor aspects.

Description

technical field [0001] The invention relates to a class of acylhydrazone compounds with antitumor activity, a preparation method and application thereof, and belongs to the technical field of medicinal chemistry. Background technique [0002] With the continuous development of medicine, people have made remarkable achievements in the treatment of many diseases. Diseases such as cancer are still a major problem plaguing the medical profession. Research on anticancer drugs is in full swing. [0003] Tumor has become the second killer that threatens human life. Among the more than 5 billion people in the world, an average of 6.9 million people die of malignant tumors every year, and 8.7 million new cases, and the number is still increasing year by year. Therefore, governments, research institutions and pharmaceutical companies of various countries have long attached great importance to tumor research and anti-tumor drugs, and significant progress has been made in the research...

Claims

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Application Information

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IPC IPC(8): C07C251/86C07C249/16C07D317/62A61K31/166A61K31/36A61P35/00
Inventor 姚志艺舒启胜夏晓明杨燕薛楠楠王庆宣
Owner SHANGHAI INST OF TECH
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