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Aryl-group-substituted acrylonitrile compound, its production and use

A technology for acrylonitrile and compounds, which is applied in the field of aryl-substituted acrylonitrile compounds and their preparation and application, and can solve the problems of high price, low toxicity and side effects, and far-reaching goals of radical tumor cure.

Inactive Publication Date: 2006-11-01
NANJING UNIV OF SCI & TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are a considerable number of anti-tumor drugs in clinical use (new drugs are still emerging), but there are still few drugs with good curative effect, low toxicity and side effects, and no cross-drug resistance, especially for the treatment of solid tumors. The difference is far, and the price is expensive, so the development of new anti-tumor drugs is still very much needed

Method used

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  • Aryl-group-substituted acrylonitrile compound, its production and use
  • Aryl-group-substituted acrylonitrile compound, its production and use
  • Aryl-group-substituted acrylonitrile compound, its production and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]Embodiment one: the synthesis of p-ethoxybenzaldehyde (formula II compound)

[0036] 1.22g p-Hydroxybenzaldehyde (10mmol), 1mL bromoethane (13.4mmol) were added in the mixed solution of 10mL toluene and 5mL water; 2 Under protection, after heating to reflux, slowly drop NaOH solution (2gNaOH dissolved in 5mL water) into it, and then continue to stir and reflux for 5-10h; after cooling, separate the organic phase, extract with 3×25mL toluene, and combine the organic phase , washed with water, and dried, the solvent was evaporated under reduced pressure to obtain p-ethoxybenzaldehyde (compound of formula II). IR(KBr)ν: 1696, 1602, 1577, 1509, 1258, 1216cm -1 .

[0037]

[0038] Formula II

Embodiment 2

[0039] Embodiment two: the synthesis of 4-(allyloxy)benzaldehyde (compound of formula III)

[0040] 2.44g p-hydroxybenzaldehyde (20mmol), 2.44g allyl bromide (20mmol), 2.76g K 2 CO 3 (20mmol) joins in 20mL acetone, stirs to make it dissolve; Under dry condition and N 2 Under protection, reflux under vigorous stirring for 5-10 hours; the reaction mixture was extracted with ethyl acetate, washed with water, dried, and evaporated to remove the organic solvent to obtain the product of yellow liquid (compound of formula III). 1 HNMR (200MHz, CDCl 3 +TMS)δ: 4.63(m, 2H), 5.30~5.40(m, 2H), 5.96~6.15(m, 1H), 7.03(m, 2H), 7.84(m, 2H), 9.89(s, 1H) ;IR(KBr)ν: 1692, 1600, 1508, 1259, 1229cm -1 .

[0041]

[0042] Formula III

Embodiment 3

[0043] Embodiment three: the synthesis of p-benzyloxybenzaldehyde (compound of formula IV)

[0044] Add 1.22g p-hydroxybenzaldehyde (10mmol), 1.70mL benzyl chloride (about 15mmol) into 18mL absolute ethanol; 2 Under protection, after heating to reflux, slowly drop NaOH ethanol solution (0.6g NaOH dissolved in 10mL absolute ethanol) into it, then continue to stir and reflux for 3-8h; distill off ethanol (and a small amount of benzyl chloride) under reduced pressure , dried in vacuo to obtain a crude product, recrystallized from absolute ethanol to obtain needle-shaped light yellow crystals, weighing 1.07 g, yield 50.47%, melting point 69-71°C. IR(KBr)ν: 1688, 1601, 1575, 1509, 1261, 1214cm -1 .

[0045]

[0046] Formula IV

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Abstract

An aryl-substituted acrylonitrile compound, its production and use are disclosed. It can be used for antineoplastic and to treat leukemia, hepatocarcinoma, gastric carcinoma and mastopathy.

Description

technical field [0001] The present invention relates to an aryl-substituted acrylonitrile compound and a preparation method thereof, as well as the use of the compound in the preparation of antitumor drugs, especially in the treatment of leukemia, liver cancer, gastric cancer and breast cancer. Background technique [0002] Malignant tumor is one of the malignant diseases that threaten human life. It is also 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, second only to cardiovascular and cerebrovascular diseases. Disease: The number of deaths due to cancer in the world is more than 5 million every year. In China, there are more than 1.6 million new cancer patients and more than 1.3 million deaths every year. Tumor treatment methods include surgery, radiation therapy, and drug therapy (chemotherapy), but chemotherapy is...

Claims

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Application Information

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IPC IPC(8): C07C255/37A61K31/277A61P35/00C07C253/30
Inventor 方志杰殷晓进高军峰丁磊王远兴韩雪莲
Owner NANJING UNIV OF SCI & TECH
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