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A kind of aminomethylpyridine derivatives and its preparation method and application

A technology of aminomethylpyridines and derivatives, which is applied in the fields of drug combination, organic chemistry, and antitumor drugs, and can solve the problem of low anti-chronic cell leukemia activity, and achieve simple post-processing methods, mild synthesis conditions, and novel structures Effect

Active Publication Date: 2019-07-02
ANHUI XINGYU CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patents CN 101503402A and CN 102225925A use the splicing principle to link imatinib intermediates with other compounds with amide bonds to obtain a series of derivatives, but these compounds have low anti-chronic cell leukemia activity

Method used

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  • A kind of aminomethylpyridine derivatives and its preparation method and application
  • A kind of aminomethylpyridine derivatives and its preparation method and application
  • A kind of aminomethylpyridine derivatives and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (E)-3-(2-Chloro-4-trifluoromethylphenyl)-2-((4-methylpyridin-3-yl)amino)ethyl acrylate

[0026] (1) Dissolve 10.8g (0.10mol) of 3-amino-4-methylpyridine, 9.50ml (0.09mol) of ethyl chloroacetate and 14.45ml (0.10mol) of triethylamine in 40ml of tetrahydrofuran, reflux for 8h, and cool to room temperature, filtered, and the filtrate was rotary evaporated under reduced pressure, and the obtained concentrated solution was dissolved in ethyl acetate, extracted with dilute hydrochloric acid (pH=2) and sodium carbonate solution (pH=12) successively, and the organic phase was rotary evaporated under reduced pressure. , recovered ethyl acetate, dried to obtain 16.1 g of a light yellow oil, and the yield was 83.0%;

[0027] (2) Dissolve 9.70g (0.05mol) of the product of step (1) in 80ml of methanol, slowly add 4.24g (0.10mol) of lithium chloride and 3.78g (0.10mol) of sodium borohydride, react at 40°C for 5h, and add bicarbonate The sodium solution was filtered, the organic phas...

Embodiment 2

[0031] (E)-3-(3,4,5-trimethoxyphenyl)-2-((4-methylpyridin-3-yl)amino)ethyl acrylate

[0032] The operation steps are the same as in Example 1, and 3,4,5-trimethoxybenzaldehyde is used in step (3) instead of 2-chloro-4-trifluoromethylbenzaldehyde to obtain the target product as a yellow solid; the purity is 98.2%; 1 H NMR (300MHz, DMSO-d 6 )δ: 8.28(s, 1H); 8.05(s, 1H); 7.67(m, 1H); 7.48(s, 1H); 7.21(m, 1H); 6.91(d, 3H); ); 4.56(m, 2H); 3.56(m, 2H); 2.31(s, 3H); 3.83(s, 6H); 3.76(s, 3H); ESI-MS m / z(%): 372.2([ M+1] + ).

Embodiment 3

[0034] (E)-3-(2-Chloro-4-trifluoromethylphenyl)-2-((5-methylpyridin-3-yl)amino)ethyl acrylate

[0035] The operation steps are the same as in Example 1, in step (1), 3-amino-5-picoline is used instead of 3-amino-4-picoline to obtain the target product as a light brown solid; the purity is 98.0%; 1 H NMR (300MHz, DMSO-d 6 )δ: 8.28(s, 1H); 8.05(s, 1H); 7.66(m, 2H); 7.30(m, 1H); 7.21(m, 1H); 6.90(d, 1H); ); 6.07(s, 1H); 4.56(m, 2H); 3.56(m, 2H); 2.23(s, 3H); ESI-MS m / z(%): 384.7([M+1] + ).

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Abstract

The invention relates to the field of drug synthesis and biological activity evaluation, in particular to an aminomethylpyridine derivative, a preparation method and application thereof. The aminomethylpyridine derivative adopts aminomethylpyridine and substituted benzaldehyde as the raw materials, and the obtained aminomethylpyridine derivative has a general structural formula shown as the specification. The aminomethylpyridine derivative provided by the invention has mild synthesis conditions, and simple and easily operable post-treatment method, thus being suitable for industrial production. Compared with the existing anti-leukemia drug imatinib, the aminomethylpyridine derivative has significant inhibitory effect on human chronic granulocytic leukemia cell line K562, and is suitable for further screening as an anti-leukemia drug.

Description

technical field [0001] The invention relates to the field of drug synthesis and biological activity evaluation, in particular to an aminomethylpyridine derivative and its preparation method and application. Background technique [0002] The Combination Principle is to combine the pharmacophore or basic structure of two drugs into the same molecule to form a new "hybrid molecule". The newly formed compound may have the properties of the two drugs and strengthen the pharmacological effect. , to reduce the toxic and side effects of the two drugs used alone; or to make the two drugs complement each other, each exerting its pharmacological effects, and synergistically curing the disease. The combination principle provides new theories and methods for the rational and efficient development of new drug molecules. Under the guidance of these theories, many new drugs designed and developed have entered the clinical stage or even entered the market. These new drugs generally have the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/74A61P35/02
CPCC07D213/74
Inventor 张升张宽宇金文艺李静
Owner ANHUI XINGYU CHEM
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