Erlotinib derivative with antitumor activity, and preparation method and application thereof

An anti-tumor activity, erlotinib technology, applied in anti-tumor drugs, organic chemistry, drug combination, etc., can solve the problems of less than 30% survival rate, high recurrence rate after treatment, and intrahepatic dissemination

Inactive Publication Date: 2017-05-10
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because liver cancer often has an insidious onset, the disease progresses rapidly after symptoms, intrahepatic dissemination and distant metastasis are very likely to occur, and the recurrence rate after treatment is also quite high. Therefore, the overall curative effect is not good, and the 5-year survival rate is less than 30%. Chinese people's health has caused great harm
However, there is no relevant record about erlotinib linked to 1,2,3-triazole compounds, nor is there any relevant record about the antitumor activity of this type of compound

Method used

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  • Erlotinib derivative with antitumor activity, and preparation method and application thereof
  • Erlotinib derivative with antitumor activity, and preparation method and application thereof
  • Erlotinib derivative with antitumor activity, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] In a 500mL multi-neck flask, add 16.8g (0.1mol) of 3,4-dimethoxybenzyl alcohol, then add 150g of acetic anhydride, and slowly add 6g of nitric acid dropwise when the temperature is lowered to about 0℃. The reaction solution is slowly stirred and the addition is complete. After the temperature was raised to room temperature, after 6 hours of reaction, the acetic anhydride was evaporated under reduced pressure, 300 mL of distilled water was added, and saturated sodium carbonate solution was slowly added dropwise to adjust the pH of the reaction solution to neutral, the reaction solution was extracted three times with 200 mL of dichloromethane, and the organic Phase, the solvent was evaporated to obtain 20 g of 2-nitro-4,5-dimethoxybenzyl alcohol.

Embodiment 2

[0033]

[0034] In a 500mL reaction flask with a stirrer, add 20g (0.093mol) of 2-nitro-4,5-dimethoxybenzyl alcohol to 150mL of benzene, then add 15g of potassium permanganate, and stir well. Then add 1.5 g of copper sulfate pentahydrate and 5 g of potassium hydroxide, and heat to reflux for reaction. After 10 hours of reaction, TLC monitors the completion of the raw material reaction. Pour the reaction solution into 500 mL of ice water. After stirring for 1 hour, adjust the reaction solution with glacial acetic acid. The pH was 9, the reaction solution was extracted three times with 200 mL of chloroform, the organic phases were combined, and the solvent was evaporated to obtain 13 g of 2-nitro-4,5-dimethoxybenzoic acid.

Embodiment 3

[0036]

[0037] In a 500mL reaction flask with a stirrer, add 16g of 2-nitro-4,5-dimethoxybenzoic acid to 150mL of solvent methanol, then add 105g of hydrazine hydrate and 0.4g of Raney nickel, and react under nitrogen protection. The system was heated to 50°C for reaction. After 5 hours of reaction, TLC monitored the completion of the raw material reaction. The reaction solution was filtered and the solvent methanol was evaporated to obtain 11 g of 2-amino-4,5-dimethoxybenzoic acid.

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Abstract

The invention discloses an erlotinib derivative with antitumor activity, and a preparation method and application thereof, and belongs to the technical field of synthesis of antitumor active medicine. The method has the main technical scheme that the erlotinib derivative with antitumor activity has a structure formula shown as the accompanying drawing, wherein R is phenyl, p-methylphenyl, m-nitrophenyl, o-chlorphenyl or o-hydroxy benzon phenyl. The invention also discloses a concrete synthesis process of the erlotinib derivative with antitumor activity and application of the erlotinib derivative with antitumor activity to preparation of liver cancer treatment medicine. The erlotinib molecules are modified and are structurally connected with a series of different 1,2,3-triazole groups; the synthesized erlotinib derivative is subjected to anti-tumor activity test; the test result shows that the compound has high inhibition activity on liver cancer HepG2 cells.

Description

Technical field [0001] The invention belongs to the technical field of synthesis of drugs with antitumor activity, and specifically relates to an erlotinib derivative with antitumor activity and a preparation method and application thereof. Background technique [0002] Liver cancer is one of the common malignant tumors in China, and the mortality rate ranks second in malignant tumors. Since liver cancer often has an insidious onset, the disease progresses rapidly after symptoms, intrahepatic dissemination, distant metastasis, etc. are very easy to occur, and the recurrence rate after treatment is also quite high. Therefore, the overall curative effect is not good, and the 5-year survival rate is less than 30%. Chinese people's health is causing great harm. At present, surgery is still the first choice for the treatment of liver cancer, but the characteristics of easy recurrence and metastasis after surgery greatly affect its efficacy and prognosis. For patients with local progr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12A61K31/517A61P35/00A61P1/16
CPCC07D403/12
Inventor 毛龙飞姜玉钦徐桂清李伟张玮玮丁清杰
Owner HENAN NORMAL UNIV
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