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Synthesis and application of imidazole selenium-containing pyrone compound

A compound, pyrone technology, applied in the fields of organic chemistry, drug combination, anti-tumor drugs, etc., can solve the problems of toxicity, humidity, expensive and so on

Inactive Publication Date: 2018-01-19
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above-mentioned vulcanizing agents used have some disadvantages, such as odor, volatility, toxicity, expensive, damp and lively and difficult to preserve

Method used

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  • Synthesis and application of imidazole selenium-containing pyrone compound
  • Synthesis and application of imidazole selenium-containing pyrone compound
  • Synthesis and application of imidazole selenium-containing pyrone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Step 1: After dissolving 4-hydroxycoumarin (1mmol) and triethylamine (1.5mmol) in 10mL of dichloromethane, cooling in a cold water bath, trifluoromethanesulfonic anhydride (1.5mmol) was slowly added dropwise to the reaction system, and the reaction After 3 hours, the solvent was removed by rotary evaporation, concentrated and purified by silica gel column separation (volume ratio of petroleum ether to ethyl acetate: 4:1) to obtain 4-trifluoromethanesulfonate-coumarin.

[0015] Step 2: Under the protection of oxygen, add 2-aminopyridine (0.5mmol), 2-thiophenethanone (10.0mmol), cuprous iodide (0.25mmol) and boron trifluoride diethyl ether (0.14mL) into 2mL of DMF solvent , reacted at 60°C for 12 hours; cooled to room temperature, extracted with ethyl acetate (30mL), dried over anhydrous sodium sulfate, and purified by concentrated silica gel column chromatography (the volume ratio of petroleum ether to ethyl acetate was 3:1) to obtain 2-(2-(Thienimidazo)[1,2-a]pyridine. ...

Embodiment 2

[0025] Activity determination of the above compounds

[0026] Experimental Materials:

[0027] 1. Human cancer cell lines: all were purchased from the Shanghai Cell Bank of the Chinese Academy of Sciences.

[0028] 2. The drug under test: After dissolving in DMSO, prepare it to an initial concentration of 10,000 mg / mL for later use.

[0029] 3. 0.9% normal saline: 250mL; 2.25g, Zhengzhou Yonghe Pharmaceutical Co., Ltd.

[0030] 4. 4-fluorouracil injection (5-Fu), specification 10mL: 0.25g / bottle, product of Shanghai Xudong Haipu Pharmaceutical Co., Ltd.:

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Abstract

The invention discloses a synthesis method and an application of an imidazole selenium-containing pyrone compound 4-((2-(thiophene-2-yl) imidazole [1,2-alpha] pyridine-3-yl) selenium yl)-2H-pyran-2-one. The method comprises the following steps: firstly, generating 4-trifluoromethane sulfonate-coumarin from the reaction of 4-hydroxyl coumarin compound and trifluoromethanesulfonic anhydride; preparing 2-(2-(thiophene imidazole) and [1,2-alpha] pyridine) from 2-aminopyridine and 2-acetylthiophene under the effect of the catalyst; and synthesizing 4-((2-(thiophene-2-yl) imidazole [1,2-alpha] pyridine-3-yl) selenium yl)-2H-pyran-2-one through the spliced reaction of the two compounds. The synthesis method has the advantages that the element selenium is used as a vulcanizing agent; the method issimple in operation and high in yield; and the compound disclosed by the invention is capable of effectively restraining the growth of human cancer cells, such as, EC9706, mcf-7, mgc-803 and pc-3.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to an imidazole selenium-containing pyrone compound 4-((2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-yl)selenoyl) -Synthesis of 2H-pyran-2-ones and their potential application as effective scaffolds for new anticancer drugs. Background technique [0002] Cancer is one of the most difficult problems in the current medical field, and the annual cancer death rate remains high. According to data from the Chinese Center for Disease Control and Prevention and the World Health Organization, at present, the death rate from cancer in China has reached 1.5 million people every year. In modern society, the burden of mental and psychological diseases is increasing, and the actual number of patients has reached 16 million. And among them. Common cancers with high mortality rates include lung cancer, liver cancer, gastric cancer, esophageal cancer, and colorectal cancer. Therefore, the research ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61P35/00
Inventor 王宏雁委旭宁刘钰郭涛孔令辉林祥斌
Owner HENAN UNIVERSITY OF TECHNOLOGY
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