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A kind of directional synthesis compound clcn and its application in anti-hepatocellular carcinoma drugs

A technology for directional synthesis and compound application in anti-tumor drugs, drug combinations, sugar derivatives, etc., can solve the problems of insignificant early symptoms of liver cancer, unsatisfactory effects, and unsuitable patients, and is conducive to industrial production and cost. Low, simple synthesis process effect

Active Publication Date: 2017-08-25
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The initial symptoms of liver cancer are not obvious, and the cure rate of advanced patients is low due to the spread of cancer cells
Surgery is a common method for the treatment of liver cancer, but most patients are not suitable for this method, and the clinical effect of non-surgical treatment is not ideal

Method used

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  • A kind of directional synthesis compound clcn and its application in anti-hepatocellular carcinoma drugs
  • A kind of directional synthesis compound clcn and its application in anti-hepatocellular carcinoma drugs
  • A kind of directional synthesis compound clcn and its application in anti-hepatocellular carcinoma drugs

Examples

Experimental program
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Effect test

Embodiment 1

[0034]Weigh 5 mg of liquiritigenin and dissolve it in 5 mL of dichloromethane solution, add 2 mL of carbon tetrabromide, then slowly add 2 mL of triphenylphosphine in dichloromethane solution dropwise in an ice bath, filter the reaction solution after the reaction is complete, and concentrate the filtrate Afterwards, reactant A was obtained by concentration and crystallization through silica gel column chromatography (petroleum ether: chloroform-2:3), with a yield of 87.8%. Weigh 2 mg of reactant A and 9 mg of KOH, place them in a dry round bottom flask, add 10 mL of tetrahydrofuran, reflux at 90 ° C for 8 h, cool to room temperature after the reaction, add p-20 mL of toluenesulfonyl chloride for 6 h, Collect the reaction liquid, remove the reaction solvent tetrahydrofuran by rotary evaporation, add water to dissolve, collect the filter residue by filtration, dry and crystallize, and obtain reactant B. The yield was 88.7%. Weigh 10mg of reactant B and 18mg of cordycepin, put ...

Embodiment 2

[0036] Weigh 4 mg of liquiritigenin and dissolve it in 4 mL of dichloromethane solution, add 1 mL of carbon tetrabromide, then slowly add 1 mL of triphenylphosphine in dichloromethane solution dropwise in an ice bath, filter the reaction solution after the reaction is complete, and concentrate the filtrate Afterwards, reactant A was obtained by concentrated crystallization through silica gel column chromatography (petroleum ether: chloroform-2:3), and the yield was 86.8%. Weigh 2mg of reactant A and 8mg of KOH, put them in a dry round bottom flask, add 5mL of tetrahydrofuran, reflux at 70°C for 5h, cool to room temperature after the reaction, add p-20mL of toluenesulfonyl chloride for 6h, Collect the reaction liquid, remove the reaction solvent tetrahydrofuran by rotary evaporation, add water to dissolve, collect the filter residue by filtration, dry and crystallize, and obtain reactant B. The yield was 88.5%. Weigh 10mg of reactant B and 18mg of cordycepin, put them in a dry...

Embodiment 3

[0038] Weigh 5 mg of liquiritigenin and dissolve it in 6 mL of dichloromethane solution, add 2 mL of carbon tetrabromide, then slowly add 2 mL of triphenylphosphine in dichloromethane solution dropwise in an ice bath, filter the reaction solution after the reaction is complete, and concentrate the filtrate Afterwards, reactant A was obtained by concentrated crystallization through silica gel column chromatography (petroleum ether: chloroform-2:3), and the yield was 88.1%. Weigh 2 mg of reactant A and 8 mg of KOH, place them in a dry round-bottomed flask, add 8 mL of tetrahydrofuran, reflux at 90 ° C for 4 h, cool to room temperature after the reaction, add p-20 mL of toluenesulfonyl chloride for 6 h, Collect the reaction liquid, remove the reaction solvent tetrahydrofuran by rotary evaporation, add water to dissolve, collect the filter residue by filtration, dry and crystallize, and obtain reactant B. The yield was 88.9%. Weigh 10mg of reactant B and 18mg of cordycepin, put t...

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Abstract

The invention provides a compound CLCN based on oriented synthesis, and further provides application of the compound to anti-liver cancer drugs. The new product CLCN is obtained through oriented synthesis by using cordycepin and liquiritigenin as raw materials, and the compound can be used as a pharmacodynamics active ingredient to be made into an anti-liver cancer medicament. The medicament can be used for treating liver cancers, has the characteristics of being remarkable in anticancer effect, quick to take effect, small in side effects and the like, and is an excellent anti-liver cancer drug candidate.

Description

technical field [0001] The invention discloses a directional synthesis compound CLCN, and further provides the application of the compound in anti-liver cancer drugs, which belongs to the technical field of pharmaceutical synthesis. Background technique [0002] Liver cancer refers to malignant tumors that occur in the liver, including primary liver cancer and metastatic liver cancer. People usually refer to primary liver cancer when they say liver cancer. The initial symptoms of liver cancer are not obvious, and the cure rate of advanced patients is low due to the spread of cancer cells. Surgery is a common method for the treatment of liver cancer, but most patients are not suitable for this method, and the clinical effect of non-surgical treatment is not satisfactory. In recent years, the anti-tumor activity of traditional Chinese medicine compound and natural compounds has become a research hotspot. Therefore, researchers hope to take this opportunity to find safer and m...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/16C07H1/00A61P35/00
CPCC07H1/00C07H19/16
Inventor 王迪逯家辉周毓麟孟庆繁滕利荣张洋孟令军权宇彤姜丹
Owner JILIN UNIV
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