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A kind of 4-(1-substituted phenylvinyl) biphenyl derivative and its preparation method and application

A technology of phenylvinyl and derivatives, applied in the field of medicine, can solve the problems of single tumor inhibitory spectrum and prone to drug resistance

Inactive Publication Date: 2016-03-23
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since tumor is a multi-stage complex disease involving multiple genes and influenced by multiple signals, in the clinical treatment of tumors, single-target anti-tumor drugs show a single tumor inhibitory spectrum and are prone to drug resistance.

Method used

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  • A kind of 4-(1-substituted phenylvinyl) biphenyl derivative and its preparation method and application
  • A kind of 4-(1-substituted phenylvinyl) biphenyl derivative and its preparation method and application
  • A kind of 4-(1-substituted phenylvinyl) biphenyl derivative and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 14

[0066] Preparation of Example 14'-(1-(4-methoxyphenyl)vinyl)-2-nitrobiphenyl (compound 1 in Table 1)

[0067]

[0068] (1) Preparation of intermediate: 2-nitro-4'-acetyl-1,1'-biphenyl (Ⅱ)

[0069] p-Acetophenoneboronic acid (0.23g, 1.4mmol), 2-nitrobromobenzene (I) (0.20g, 1mmol), cesium carbonate (0.489g, 1.5mmol) dissolved in water (0.75ml) and dioxane ( 2.2ml), then added bis(triphenylphosphine)palladium chloride (0.02g, 0.03mmol), under nitrogen protection, refluxed and stirred at 100°C for 1hr, the reaction solution was a brown clear liquid. The reaction solution was slowly added to crushed ice (400g), then stirred for 1h. Add 15ml of water, extract with ethyl acetate (10ml×3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (PE:EtOAc=20:1) to obtain a white solid, Yield 86%. Obtain intermediate (II);

[0070] (2) Preparation of intermediate: 2-nitro-4'-acetyl-1,1'-bip...

Embodiment 2-7

[0075] Repeat Example 1, the difference is: using different raw materials, thereby preparing compound 2-7. details as follows:

[0076] 3-methyl bromobenzene, 2-methoxy bromobenzene, 3-methoxy bromobenzene, 4-nitrobromobenzene, 3-nitrobromobenzene, 2-methyl bromobenzene and p-acetylphenylboronic acid respectively Prepare the corresponding substituted p-acetylbiphenyl, and then make the corresponding substituted 4'-acetyl-1,1'-biphenyl p-toluenesulfonylhydrazone with p-toluenesulfonyl hydrazide, and finally mix with p-methoxy bromide Benzene reacts to generate compounds 2, 3, 4, 5, 6, and 7 in Table 1.

Embodiment 8

[0077] Example 8: Preparation of 4'-(1-(3-acetoxy-4-methoxyphenyl)vinyl)-3,5-dimethoxybiphenyl (compound 8 in Table 1)

[0078]

[0079] (1) Preparation of intermediate: 3,5-dimethoxy-4'-acetyl-1,1'-biphenyl (VII)

[0080] p-Acetophenoneboronic acid (0.23g, 1.4mmol), 3,5-dimethoxybromobenzene (VI) (0.22g, 1mmol), cesium carbonate (0.489g, 1.5mmol) were dissolved in water (0.75ml) and di Oxycycline (2.2ml) and bis(triphenylphosphine)palladium chloride (0.02g, 0.03mmol) were added, under nitrogen protection, and stirred at reflux at 100°C for 1hr, the reaction solution was a brown clear liquid. The reaction solution was slowly added to crushed ice (400g), then stirred for 1h. Add 15ml of water, extract with ethyl acetate (10ml×3), combine the organic phases, dry over anhydrous sodium sulfate, filter, concentrate under reduced pressure, and separate by column chromatography (PE:EtOAc=20:1) to obtain a white solid, Yield 86%. Intermediate (VII) is obtained;

[0081] (2) P...

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Abstract

The invention relates to a 4-(1-substituted phenylvinyl) biphenyl derivative and a preparation method and application thereof. The general structural formula of the 4-(1-substituted phenylvinyl) biphenyl derivatives is: the 4-(1-substituted phenylvinyl) biphenyl derivatives of the present invention can be used to prepare tubulin inhibitors, Protein kinase inhibitors, drugs for the treatment of various cancers that respond to cytotoxic activity, such as breast or colon, and disease cancers associated with abnormal angiogenesis, are characterized by high efficiency, low toxicity, and multiple inhibitory effects.

Description

Technical field [0001] The invention involves the field of pharmaceutical technology. Specifically, it is a 4- (1-replacement of benzyl ethylenel) and the preparation methods and applications. Background technique [0002] In recent years, malignant tumors have become the first cause of death in urban and rural residents in my country, and the mortality rate has grown.Today's chemotherapy drugs are the main methods for treating tumors. Among them, molecular targeted drugs have a more clear mechanism, higher specificity, and low toxicity than traditional cytotoxic anti -tumor drugs.EssenceBecause tumors are multi -gene participation and multi -stage complex diseases that affect multiple signals, during the clinical treatment of tumors, single -target anti -tumor drugs show the problem of tumor curiosity, prone to drug resistance.Anti -tumor drugs that act on multiple targets can effectively cut off multiple tumors. It has better treatment advantages. At the same time, it can avoid...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07B37/00C07C201/12C07C205/35C07C67/293C07C69/157C07C41/18C07C43/23C07C227/18C07C229/08C07C209/62C07C211/52C07C231/12C07C233/15C07C253/30C07C255/55C07C255/54C07C233/43C07C213/00C07C213/08C07C215/74C07C217/80C07C209/68C07C211/45C07C211/50A61K31/085A61K31/222A61K31/09A61K31/223A61K31/136A61K31/167A61P35/00A61P35/02
Inventor 周有骏孙囡囡朱驹吕加国郑灿辉蒋骏航
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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