Method for synthesizing anti-form stilbene compounds and application of method in preparing anti-tumor medicines

A technology of stilbene compounds and anti-tumor drugs, which is applied in the field of synthesizing trans-stilbene compounds, can solve the problems of reduced yield, difficult separation, and difficulty in obtaining compounds, and achieves the effects of simple method, reduced cost, and increased difficulty

Inactive Publication Date: 2012-07-11
NORTHEAST FORESTRY UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the current synthetic method still has two unsatisfactory places. First, the number and types of substituents are limited by aldehydes, and it is difficult to obtain compounds with multiple substituents and different substituents; second, most Coupling reactions generate cis-trans isomers at the same time, resulting in lower yields and difficulties in separation

Method used

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  • Method for synthesizing anti-form stilbene compounds and application of method in preparing anti-tumor medicines
  • Method for synthesizing anti-form stilbene compounds and application of method in preparing anti-tumor medicines
  • Method for synthesizing anti-form stilbene compounds and application of method in preparing anti-tumor medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033](1) Preparation of acetoacetylnonylamine: Dissolve 20mmol of nonylamine in 50ml of water, cool down to 0°C, add 20mmol of diketene dropwise within 1 hour, react for 2 hours after dropping, extract with dichloromethane, wash the organic layer with water, and dry , filtered with suction, concentrated to dryness under reduced pressure to obtain acetoacetylnonylamine with a yield of 96%;

[0034] (2) Preparation of 2-(bis(methylthio)methenyl)-N-nonyl-3-oxobutanamide: 20mmol of acetoacetylnonylamine obtained in the previous step was dissolved in 50ml of N,N-dimethyl In base formamide, cool down to 0°C, add 50mmol potassium carbonate, stir at 0°C for 30min, then add 24mmol carbon disulfide, react at 0°C for 1 hour, then add 40mmol methyl iodide dropwise within 30min, rise to React at 10-35°C for 4 hours, pour into water, a yellow solid precipitates out, filter with suction, wash with water, and dry to obtain 2-(di(methylthio)methenyl)-N-nonyl-3-oxobutyramide , yield 88%;

[...

Embodiment 2

[0038] (1) Preparation of acetoacetylnonylamine: Dissolve 20mmol of nonylamine in 50ml of benzene, cool to 0°C, add 20mmol of diketene dropwise within 1 hour, react for 2 hours after dropping, wash the organic layer with water, dry, and suction filter. Concentrated to dryness under reduced pressure to obtain acetoacetylnonylamine with a yield of 93%;

[0039] (2) Preparation of 2-(bis(methylthio)methenyl)-N-nonyl-3-oxobutanamide: 20mmol of acetoacetylnonylamine obtained in the previous step was dissolved in 50ml of N,N-dimethyl In base formamide, cool down to 0°C, add 50mmol potassium carbonate, stir at 0°C for 30min, then add 24mmol carbon disulfide, react at 0°C for 1 hour, then add 40mmol methyl iodide dropwise within 30min, rise to 10 React at ~35°C for 4 hours, pour into water, a yellow solid precipitates, filter with suction, wash with water, and dry to obtain 2-(di(methylthio)methenyl)-N-nonyl-3-oxobutyramide, Yield 88%;

[0040] (3) (4E,6E)-2-(di(methylthio)methenyl)...

Embodiment 3

[0043] (1) Preparation of acetoacetylmorpholine: Dissolve 20mmol morpholine in 50ml benzene, cool to 0°C, add 20mmol diketene dropwise within 1 hour, react for 2 hours after dropping, wash the organic layer with water, dry, and suction filter, Concentrated to dryness under reduced pressure to obtain acetylacetylmorpholine with a yield of 89%;

[0044] (2) Preparation of 2-(bis(methylthio)methenyl)-1-morpholinyl-1,3-butanedione: 20mmol of acetylacetylmorpholine obtained in the previous step was dissolved in 50ml N,N- In dimethylformamide, cool down to 0°C, add 50mmol potassium carbonate, stir at 0°C for 30min, then add 24mmol carbon disulfide, react at 0°C for 1 hour, then add 40mmol methyl iodide dropwise at about 30min, after the addition is complete Rise to 10-35°C for 4 hours, remove N,N-dimethylformamide, extract with dichloromethane, wash with water, dry, filter with suction, concentrate under reduced pressure to dryness, and obtain 2-(bis(methylthio)methylene Base)-1-mo...

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Abstract

The invention discloses a method for synthesizing an anti-form stilbene compound and the application of the method in preparing anti-tumor medicines. According to the method, diketene and amine are in full reaction to compound N-substituent-3-oxobutanamide; then N-substituent-3-oxobutanamide is reacted with carbon disulfide and methyl iodide successively through one-pot reaction to compound alpha-oxo ketene dithioacetals; further, the alpha-oxo ketene dithioacetals is in condensation with replacement cinnamyl aldehyde to obtain alpha-((2E.4E)-5-aryl-2, 4-pentylene acyl) ketenedithioacetals; and finally, the anti-form stilbene compound is obtained through <5+1> aromatization reaction. Compared with the traditional method, according to the method, cis-isomer is avoided, the synthetic production and the utilization ratio of raw materials are high, the raw materials are chip and easy to obtain, the method and processing equipment are simple and feasible, and mass production is easy to realize. A stilbene derivative in this method has a notable restriction effect on multiple cancer cells, so that the stilbene derivative can be used for preparing the anti-tumor medicines, and the method has a high medical value and a wide market prospect.

Description

technical field [0001] The invention relates to a method for synthesizing trans-stilbene compounds and its application in the preparation of antitumor drugs. Background technique [0002] Stilbene compounds are a general term for a class of compounds with stilbene as the structural core, including stilbene, diphenylethyl, phenanthrene and their derivatives. Stilbene compounds are mainly distributed in the parenchyma of plants. The first natural stilbene compound was isolated from the Polygonaceae plant Rhubarb in 1822. [0003] In recent years, with the emergence of environmental problems and various pollutions, the incidence of cancer is far greater than before. This situation has prompted scientists to intensify research on anticancer drugs. Polyhydroxy stilbene compounds are currently the most widely and deeply studied stilbene compounds with various biological activities. Resveratrol is one of the representative compounds. Early studies have shown that resveratrol has...

Claims

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Application Information

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IPC IPC(8): C07C321/28C07C319/14C07D295/192A61K31/166A61K31/5375A61P35/00
Inventor 付玉杰余平
Owner NORTHEAST FORESTRY UNIVERSITY
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