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N-(4-(4-(pyridine-2-radical) piperazine-1-radical) pyrimidine-2-radical) amide and salt and preparation method and application thereof

A technology of pyridine and piperazine, applied in the field of chemical synthesis of drugs, can solve problems such as limited types and unsatisfactory cancer treatment effects

Inactive Publication Date: 2013-01-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The object of the present invention is to provide a kind of N-(4-(4- (Pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)amides or pharmaceutically acceptable salts thereof

Method used

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  • N-(4-(4-(pyridine-2-radical) piperazine-1-radical) pyrimidine-2-radical) amide and salt and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0056] Example 1 N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-2-chlorothiazole-5-amide compound

[0057] The preparation method of N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-2-chlorothiazole-5-amide compound in this embodiment comprises the following steps:

[0058] Step 1. Preparation of 2-amino-4-(4-(pyridin-2-yl)piperazine)pyrimidine

[0059] Add 0.6475g (5mmol) 2-amino-4-chloropyrimidine, 2.9340g (15mmol) 4-(pyridin-2-yl)piperazine, 9.5ml N, N-dimethylbenzylamine and 50ml of anhydrous pyridine were reacted at 20° C. for 24 hours under stirring, during which the degree of reaction was monitored by thin-layer chromatography. Filter after the reaction, the organic phase is first washed with 1M NaOH solution, then washed with distilled water until the organic phase is neutral, and finally anhydrous MgSO is added to the organic phase 4 Dry overnight, filter, after concentrating the filtrate, recrystallize with ethyl acetate, filter, collect the white powder ...

Embodiment 2

[0065] Example 2 Inhibitory effect of N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)amide compounds or pharmaceutically acceptable salts thereof on cancer cells

[0066] In this example, lung cancer cell line A549, liver cancer cell line Bel-7402, gastric cancer cell line SGC7901 and nasopharyngeal carcinoma cell line CNE2 were used as experimental subjects, and 2-amino-4-(4-(pyridin-2-yl)piper oxazine)pyrimidine, N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-thiazole-5-amide, N-(4-(4-(pyridine- 2-yl)piperazin-1-yl)pyrimidin-2-yl)-2,4-dimethylthiazole-5-amide, N-(4-(4-(pyridin-2-yl)piperazine-1 -yl)pyrimidin-2-yl)-4-methylthiazole-5-amide, N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-2 -Phenyl-4-methylthiazole-5-amide, N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-2-(pyridine-3- Base)-4-methylthiazole-5-amide, N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)-2-(4-chlorophenyl )-4-methylthiazole-5-amide, N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyri...

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Abstract

The invention discloses an N-(4-(4-(pyridine-2-radical) piperazine-1-radical) pyrimidine-2-radical) amide of a structural formula (I). When X2 is -CH3, X1 is taken from one of -H, -CH3 or -Br arbitrarily; when X2 is -H, X1 is taken from one of -H, -Br and -CI arbitrarily; X3 is taken from -H or one of -H arbitrarily; and X4 is taken from -H. Organic salt or inorganic salt such as hydrochloride, sulfate, phosphate, mesylate, sulfonate, formate, acetate, malate or lactate acceptable in pharmacy is provided. The invention further relates to a preparation method of the compound and application of the compound and the salt acceptable in the pharmacy in preparation of antineoplastic drugs and particularly in preparation of drugs for treating lung cancer, liver cancer, gastric cancer and nasopharynx cancer.

Description

technical field [0001] The invention relates to the technical field of chemically synthesized drugs, in particular to a class of organic small molecule N-(4-(4-(pyridin-2-yl)piperazin-1-yl)pyrimidin-2-yl)amide compounds or their pharmaceutical preparations Acceptable salts and their preparation methods and their application in the preparation of antitumor drugs. Background technique [0002] Cancer is one of the major diseases that seriously endanger human health. In my country, the number of deaths due to cancer is more than 1 million every year, and it is increasing year by year. It has become the second largest killer of human beings after cardiovascular disease. At present, the treatment of cancer mainly includes surgical treatment, radiotherapy, chemotherapy and other methods, among which chemotherapy plays an important role in the treatment of cancer. [0003] Traditional anticancer drugs are mainly cytotoxic drugs. This type of anticancer drugs mainly acts on cellula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/14A61P35/00
Inventor 刘芳谢晓琼何经纬王忠雨黄唯燕刘伟廖速波
Owner SOUTH CHINA UNIV OF TECH
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