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1-cyan-1-(3, 5-dimethoxy phenyl)-2-(4-r group phenyl ethane and preparation method

A technology of dimethoxyphenyl and phenylphenyl, applied in the field of organic chemistry and medicinal chemistry, can solve the problems of reducing the expression of cell cyclin protein, cell apoptosis, failure to complete, etc.

Inactive Publication Date: 2005-10-26
JIANGSU INST OF NUCLEAR MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
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AI Technical Summary

Problems solved by technology

[0012] In 2001, Ahmad et al. [Ahmad N, Adhami VM, Afaq, et al. Resveratrol causes WAF-1 / p21-mediated G(I)-phase arrest of cell cycle and induction of apoptosis inhuaman epidermoid careinoma A431 cells. Clin Cancer Res, 2001 , 7(5):1466] reported that resveratrol can induce the cyclin-dependent protein kinase (CDK) inhibitory protein p21 WAF-1 , and can reduce the protein expression of cyclin D1, D2, E and CDK2, CDK4, CDK6, and then cause the G of human epidermal cancer A431 cells 1 phase pause so that the cell cannot complete the transition from G 1 Phase to S phase transformation, and this process is considered irreversible, will eventually lead to apoptosis
But as a cancer drug, resveratrol is not strong enough

Method used

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  • 1-cyan-1-(3, 5-dimethoxy phenyl)-2-(4-r group phenyl ethane and preparation method
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  • 1-cyan-1-(3, 5-dimethoxy phenyl)-2-(4-r group phenyl ethane and preparation method

Examples

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Effect test

Embodiment 1

[0032] Example 1: Preparation of 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene

[0033] 3, the preparation of 5-dimethoxyphenylacetonitrile (1):

[0034] Add 9.8 grams of sodium cyanide and 50 milliliters of water into a 250 milliliter three-necked flask, stir to dissolve the solid, add 50 milliliters of absolute ethanol, raise the temperature to 65°C, add 40 grams of 3,5-dimethoxybenzyl bromide, and The reaction was incubated for 1.5 hours. Pour out the reaction solution, cool to room temperature and precipitate a solid, filter to obtain a crude product, recrystallize from methanol / water to obtain 23 g of white needle-like crystals, melting point 51-53°C.

[0035] Preparation of 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-methoxyphenyl)ethene (2a):

[0036] In a 150 ml three-necked flask, 3.54 g of 3,5-dimethoxyphenylacetonitrile (1), 2.72 g of p-methoxybenzaldehyde and 20 ml of methanol were added. Stir and heat up to 60°C, and add 1 g of sodium methoxide. The react...

Embodiment 2

[0037] Example 2: Preparation of 1-cyano-1-(3,5-dimethoxyphenyl)-2-phenylethylene (2b)

[0038] Using a method similar to Example 1, by 3.54 grams of 3,5-dimethoxyphenylacetonitrile (1) and 2.12 grams of benzaldehyde and 20 milliliters of methanol, 1 gram of sodium methylate, react to obtain 1-cyano-1- (3,5-dimethoxyphenyl)-2-phenylethene (2b) 2.4 g, melting point 68-70°C.

Embodiment 3

[0039] Example 3: Preparation of 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-nitrophenyl)ethene (2c)

[0040] Adopt the similar method of embodiment 1, by 3.54 grams of 3,5-dimethoxyphenylacetonitrile (1) and 3 grams of 4-nitrobenzaldehyde and 20 milliliters of methanol, 1 gram of sodium methylate, react to obtain golden yellow crystals 5.5 g of 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-nitrophenyl)ethene (2c), melting point 214-216°C.

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Abstract

The present invention relates to 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-R group phenyl) ethylene and its preparation method. Said invention also provides the general formula of said compound. Said product is 1,2-diphenylethene derivative, analogue of Pterostibene, and can be used in the medicine field for resisting tumor and resisting oxidation.

Description

technical field [0001] 1-cyano-1-(3,5-dimethoxyphenyl)-2-(4-Rylphenyl)ethene and its preparation method relate to a class of 1,2-stilbene derivatives, It belongs to the field of organic chemistry and medicinal chemistry. Background technique [0002] In 1989, the results of the epidemiological survey of the World Cardiovascular Disease Control System hosted by the World Health Organization (WHO) showed that the morbidity and mortality of coronary heart disease in the French were lower than those in other western countries, especially the Americans and the British. much. Although the French consume almost four times as much saturated fat as Americans and Britons, their risk of heart disease is only one-third that of the latter. This phenomenon is known as the "French Paradox". Studies have shown that this phenomenon is closely related to France being the world's largest wine producer and consumer. Analyzing the reason, it may be because there is a substance called resvera...

Claims

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Application Information

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IPC IPC(8): C07C255/34
Inventor 罗世能朱玉松沈永嘉谢敏浩邹霈刘娅灵何拥军
Owner JIANGSU INST OF NUCLEAR MEDICINE
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