Conjugated diene derivatives, preparation method thereof and use as anticancer drug

A technology of conjugated dienes and derivatives, which is applied in drug combinations, antineoplastic drugs, organic chemistry, etc., can solve the problems of prolonging the survival time of cancer patients and not being able to completely cure cancer, and achieve the ability to inhibit the growth of tumor cells. The effect of being simple and easy to implement and having broad application prospects

Active Publication Date: 2016-03-02
HUBEI BIOPESTICIDE ENG RES CENT +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the advancement of society's science and technology, human beings' understanding of cancer has gradually become clearer, and the methods, technologies and theories for the prevention and early diagnosis of certain cancers have also become more mature, but they cannot completely cure cancer, and can only prolong the life of cancer in a very limited way. patient survival time

Method used

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  • Conjugated diene derivatives, preparation method thereof and use as anticancer drug
  • Conjugated diene derivatives, preparation method thereof and use as anticancer drug
  • Conjugated diene derivatives, preparation method thereof and use as anticancer drug

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Experimental program
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Effect test

Embodiment 1

[0032] The structure of the partial conjugated diene derivative of the present invention is one of the specific compounds listed in Table 1:

[0033] Table 1: List of representative compound structures of general formula I

[0034]

[0035]

[0036]

[0037]

[0038]

Embodiment 2

[0040] Compound 2-(benzo[d]thiazol-2-yl)-4-(1-(phenyl)imidazoline-2-ylidene)-4-nitrobutyl- 2-alkene nitrile, its preparation method is:

[0041]

[0042] Using N-phenylethylenediamine as the starting material, referring to the method disclosed in the patent WO2004058714A1, successively undergoes a substitution reaction with 1,1-dithiomethyl-2-nitroethylene, and then reacts with N,N-dimethyl The intermediate 2-(1-(phenyl)imidazolin-2-ylidene)-2-nitroacetaldehyde (M-1) was prepared by condensation reaction of methyl formamide dimethyl acetal and alkaline hydrolysis reaction. Then weigh M-1, that is, 2-(1-(phenyl)imidazoline-2-ylidene)-2-nitroacetaldehyde 0.12g (0.5mmol) and dissolve it in 10mL absolute ethanol. Add 0.096g (0.55mmol) of 2-cyanomethylbenzothiazole (compound A) and a catalytic amount of potassium hydroxide, stir the reaction mixture at room temperature for 30 minutes, then slowly heat to 40-45°C, keep warm for reaction, and monitor by TLC until the reaction is...

Embodiment 3

[0044] Compound 2-(benzo[d]oxazol-2-yl)-4-(1-((6-chloropyridin-3-yl)methyl)imidazoline-2 numbered as I-37 in Example 1 -subunit)-4-nitrobut-2-enenitrile, its preparation method is:

[0045]

[0046] Using 2-chloro-5-chloromethylpyridine as the starting material, it undergoes the substitution reaction with ethylenediamine, the substitution reaction with 1,1-dithiomethyl-2-nitroethylene, and then with N,N -Dimethylformamide dimethyl acetal condensation reaction, alkaline hydrolysis reaction to prepare intermediate 2-(1-((6-chloropyridin-3-yl)methyl)imidazoline-2-ylidene)-2 - Nitroacetaldehyde (M-2). Then weigh M-2, 0.14g (0.5mmol) of 2-(1-((6-chloropyridin-3-yl)methyl)imidazolin-2-ylidene)-2-nitroacetaldehyde in 10mL In absolute ethanol, at room temperature, 0.087 g (0.55 mmol) of 2-cyanomethylbenzoxazole (compound B) and a catalytic amount of piperidine were added successively, and the reaction mixture was first stirred at room temperature for 30 minutes, and then slowly h...

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Abstract

Disclosed are conjugated diene derivatives, preparation method therefor, and uses thereof as anticancer drug. The structures of the conjugated diene derivatives are represented by general formula (I). Practices prove that the compounds have an activity of distinctly inhibiting the growth of tumor cells, and that the antitumor activity of some preferred compounds is distinctly superior to control drug. Furthermore, the preparation process for the compounds is simple and very practicable; raw materials can be easily obtained; the compounds are antitumor active substances having broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of organic drug synthesis, and specifically relates to a conjugated diene derivative, a preparation method thereof and an application as an anticancer drug. Background technique [0002] Antineoplastic drugs refer to drugs against malignant tumors, also known as anticancer drugs. Malignant tumor is a common and frequently-occurring disease that seriously threatens human health. The mortality rate of human beings caused by malignant tumors ranks second among all diseases, becoming the second "killer" after cardiovascular diseases. At the beginning of 2013, the latest edition of the "2012 China Cancer Registration Annual Report" released by the National Cancer Registration Center indicated that there were about 3.12 million new cancer cases in China each year, and more than 2 million deaths due to cancer, which means that 6 people were diagnosed every minute for cancer. At present, the incidence of cancer in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D413/14C07D401/14C07D401/06C07D417/14C07D417/12A61P35/00
CPCA61P35/00C07D213/61C07D233/26C07D401/06C07D401/14C07D403/06C07D413/06C07D413/12C07D413/14C07D417/06C07D417/12C07D417/14
Inventor 柯少勇杨自文石丽桥刘曼莉王开梅梁英江爱兵
Owner HUBEI BIOPESTICIDE ENG RES CENT
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