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Tricyclic furo[2, 3-d]pyrimidone compounds and application thereof

A compound, 3-D technology, applied in drug combination, organic chemistry, antineoplastic drugs, etc.

Active Publication Date: 2021-07-13
XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on finding anti-cancer active ingredients with low toxicity and high curative effect from natural animals and plants. Therefore, chemically synthesized anti-cancer drugs are still one of the hotspots of domestic and foreign scientists in recent years.

Method used

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  • Tricyclic furo[2, 3-d]pyrimidone compounds and application thereof
  • Tricyclic furo[2, 3-d]pyrimidone compounds and application thereof
  • Tricyclic furo[2, 3-d]pyrimidone compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Preparation of Compounds A1-A9:

[0098] At 0°C, add 30g, 0.44mol of sodium ethoxide into 50g, 0.44mol of ethyl cyanoacetate, and stir for 30 minutes at 0°C, then dropwise add 0.30mol of chloroacetone with different substituents , reacted at room temperature until all the raw materials disappeared, the reaction liquid was concentrated, washed with brine, extracted with ethyl acetate, dried over anhydrous sodium sulfate, dried over anhydrous sodium sulfate, and concentrated again to obtain compounds A1-A9 respectively.

Embodiment 2

[0100] Preparation of Compounds B1-B9:

[0101] Dissolve 50 mmol of compound A1-A9 obtained in Example 1 in 50 mL of trifluoroacetic acid, react at room temperature until all raw materials disappear, concentrate the reaction solution, wash with saturated saline, saturated aqueous sodium bicarbonate, extract with ethyl acetate, anhydrous sulfuric acid Drying over sodium and concentrating afforded compounds B1-B9, respectively.

Embodiment 3

[0103] Preparation of compound C1:

[0104] Dissolve 11.69g, 10mmol of compound B obtained in Example 2 in 20mL of anhydrous dioxane, add 1.02g, 12mmol of 2-pyrrolidone, then slowly dropwise add 1.40mL, 15mmol of phosphorus oxychloride, and reflux to react to the raw material All disappeared, the reaction solution was concentrated, washed with saturated saline, saturated aqueous solution of sodium bicarbonate, extracted with ethyl acetate, dried over anhydrous sodium sulfate, concentrated again, and eluted by column chromatography, the column chromatography silica gel was 200-300 mesh , the eluent is petroleum ether at a volume ratio of 1:2: ethyl acetate, and compound C1 is obtained as 2-methyl-7,8-dihydrofuro[2,3-d]pyrrolo[1,2-a ] Pyrimidin-4(6H)-one, yield: 4%, pale yellow oil;

[0105] 1 H NMR (400MHz, CDCl3) δ6.46 (s, 1H), 4.19 (t, J = 7.4Hz, 2H), 3.18 (t, J = 8.0Hz, 2H), 2.40 (s, 3H), 2.35–2.26 (m,2H); 13 C NMR (101MHz, CDCl3) δ165.08, 159.86, 157.83, 151.54, 106.41,...

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PUM

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Abstract

The invention relates to compounds. Cyanoethyl acetate and chloroacetone with different substituent groups are used as initial raw materials, a cyanoethyl ester compound is generated under the action of sodium ethoxide, then furan compounds are generated through intramolecular ring closing under the action of trifluoroacetic acid, the furan compounds respectively react with 2-pyrrolidone, valerolactam and caprolactam under the action of phosphorus oxychloride to form a ring, so as to obtain furo[2, 3-d]pyrimidinone compounds, and then oxygen-sulfur exchange is performed under the action of phosphorus pentasulfide, so as to obtain the furo[2, 3-d]pyrimidinethione compounds. The 54 kinds of obtained tricyclic furo[2, 3-d]pyrimidone compounds are used as positive control of DOX, the inhibitory activity of Hela cervical cancer cells, MCF-7 breast cancer cells and A549 lung cancer cells is achieved, and results show that the compounds C11 and C17 have the inhibitory activity of the Hela cervical cancer cells; the compounds D5 and D7 have inhibitory activity on A549 lung cancer cells; and the compound C14 has inhibitory activity on MCF-7 breast cancer cells.

Description

technical field [0001] The invention relates to a tricyclic furo[2,3-d]pyrimidinone compound and its use. The results of cell activity screening of the compound show that two compounds have inhibitory activity on Hela cervical cancer cells; one compound It has inhibitory activity on MCF-7 breast cancer cells; 2 compounds have inhibitory activity on A549 lung cancer cells. Background technique [0002] According to the statistics of the World Health Organization (WHO), there are about 10 million cancer cases worldwide each year, and about 7 million deaths. In my country, the annual cancer incidence is about 1.2 million, and the number of cancer deaths is as high as 900,000 or more. [1,2] , has become the second killer of human after cardiovascular disease. Although most of the chemically synthesized anticancer drugs also produce toxic and side effects on normal cells of the human body. However, there are few reports on finding anticancer active ingredients with low toxicity...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/147A61P35/00
CPCC07D491/147A61P35/00
Inventor 阿吉艾克拜尔·艾萨松布尔聂礼飞赵江瑜胡尔西地·博扎罗夫
Owner XINJIANG TECHN INST OF PHYSICS & CHEM CHINESE ACAD OF SCI
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