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4-(1-substituted-phenylvinyl)biphenyl derivatives, and preparation method and application thereof

A technology of phenylvinyl and substituents, applied in the field of medicine, can solve problems such as easy drug resistance and single tumor inhibitory spectrum

Inactive Publication Date: 2014-12-24
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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  • 4-(1-substituted-phenylvinyl)biphenyl derivatives, and preparation method and application thereof
  • 4-(1-substituted-phenylvinyl)biphenyl derivatives, and preparation method and application thereof
  • 4-(1-substituted-phenylvinyl)biphenyl derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Example 1 Preparation of 4'-(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-acetophenone boronic acid (0.23g, 1.4mmol), 2-nitrobromobenzene (I) (0.20g, 1mmol), cesium carbonate (0.489g, 1.5mmol) are dissolved in water (0.75ml) and dioxane ( 2.2ml), then add bis(triphenylphosphorus)palladium chloride (0.02g, 0.03mmol), protected by nitrogen, reflux and stir at 100°C for 1hr, the reaction solution is brown and clear. The reaction solution was slowly added to crushed ice (400g), and then stirred for 1h. Add 15ml of water, extract with ethyl acetate (10ml×3), combine the organic phases, dry with anhydrous sodium sulfate, filter, concentrate by distillation under reduced pressure, and separate by column chromatography (PE: EtOAc = 20:1) to obtain a white solid. The yield was 86%. Obtain intermediate (II);

[0070] (2) Preparation of intermediate: 2-nitro-4'-acet...

Embodiment 2-7

[0075] Repeat Example 1 with the difference that different raw materials are used to prepare compound 2-7. details as follows:

[0076] Combine 3-methylbromobenzene, 2-methoxybromobenzene, 3-methoxybromobenzene, 4-nitrobromobenzene, 3-nitrobromobenzene, and 2-methylbromobenzene with p-acetophenylboronic acid. Prepare into the corresponding substituted p-acetyl biphenyl, and then make the corresponding substituted 4'-acetyl-1,1'-biphenyl p-toluene sulfonyl hydrazone with p-toluenesulfonyl hydrazide, and finally with p-methoxy bromide respectively Benzene reacts to form 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-acetophenone boronic acid (0.23g, 1.4mmol), 3,5-dimethoxy bromobenzene (VI) (0.22g, 1mmol), cesium carbonate (0.489g, 1.5mmol) dissolved in water (0.75ml) and two Oxane (2.2ml), then add bis(triphenylphosphorus)palladium chloride (0.02g, 0.03mmol), under nitrogen protection, reflux and stir at 100°C for 1hr, the reaction solution was brown clear. The reaction solution was slowly added to crushed ice (400g), and then stirred for 1h. Add 15ml of water, extract with ethyl acetate (10ml×3), combine the organic phases, dry with anhydrous sodium sulfate, filter, concentrate by distillation under reduced pressure, and separate by column chromatography (PE: EtOAc = 20:1) to obtain a white solid. The yield was 86%. Obtain intermediate (Ⅶ);

[0081] (2) Preparation of i...

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Abstract

The invention relates to 4-(1-substituted-phenylvinyl)biphenyl derivatives, and a preparation method and application thereof. The structural general formula of the 4-(1-substituted-phenylvinyl)biphenyl derivatives is disclosed in the specification. The 4-(1-substituted-phenylvinyl)biphenyl derivatives can be used for preparing microtubulin inhibitors, protein kinase inhibitors and medicines for treating various cancers responding against cytotoxic activity (such as mammary cancer or colon cancer) and abnormal angiogenesis related cancers, and has the characteristics of high efficiency, low toxicity and multiplex inhibitory effects.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a 4-(1-substituted phenylvinyl) biphenyl derivative and a preparation method and application thereof. Background technique [0002] In recent years, malignant tumors have become the first cause of death among urban and rural residents in my country, and the mortality rate is increasing. Today's chemotherapy drugs are the main method to treat tumors. Among them, molecular targeted drugs have clearer mechanism of action, higher specificity, and lower toxicity than traditional cytotoxic anti-tumor drugs, and are the main direction of current anti-tumor drug research. . 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 and other problems. Antineoplastic drugs that act on multiple targets...

Claims

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Application Information

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Patent Type & Authority Applications(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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