Quercetin derivatives or analogs thereof, and application thereof

A technology of quercetin and analogues, applied in the field of medicinal chemistry, can solve the problems of high toxicity and side effects, high treatment costs, and unsatisfactory treatment effects

Inactive Publication Date: 2013-03-27
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The general treatment method is a combination of interferon and ribavirin, but the treatment effect is not ideal, and the treatment cost is expensive and the side effects are relatively large

Method used

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  • Quercetin derivatives or analogs thereof, and application thereof
  • Quercetin derivatives or analogs thereof, and application thereof
  • Quercetin derivatives or analogs thereof, and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of 7-benzyloxy-2-(3,4-dibenzyloxyphenyl)-3,5-dihydroxy-4H-benzopyran-4-one.

[0029] Reaction 1

[0030]

[0031] Dissolve 5.00g of rutin (8.2mmol) and 2.83g of potassium carbonate (20.5mmol) in 40mL of anhydrous N,N-dimethylformamide (DMF), react for 0.5h under nitrogen protection, add 3.2mL of benzyl Bromine (27.1 mmol), continued to stir the reaction at 60°C for 3h. After the reaction was completed, the reaction solution was acidified with 10% acetic acid to pH=5, a solid precipitated out, and the precipitate was collected by centrifugation. 60 mL of ethanol was added to the above precipitate, and 9 mL of concentrated hydrochloric acid was added in portions, and the reaction solution was stirred and reacted at 70° C. for 2 h. After the reaction, cool to room temperature, filter and wash the precipitated precipitate with water to obtain a crude product. The above crude product was recrystallized in a mixed solvent of dichloromethane / ethanol t...

Embodiment 2

[0032] Example 2. Synthesis of quercetin-3-O-aromatic formate compounds.

[0033] Reaction 2:

[0034]

[0035] Table 1

[0036]

[0037]

Embodiment 21

[0038] Example 2.1 Synthesis of 2-(3,4-dihydroxyphenyl)-3-benzoyloxy-5,7-dihydroxy-4H-chromen-4-one (compound 1-1).

[0039] 200mg of the product 7-benzyloxy-2-(3,4-dibenzyloxyphenyl)-3,5-dihydroxy-4H-benzopyran-4-one (0.35mmol) obtained in Example 1 With 100mg 1-ethyl-(3-dimethylaminopropyl) carbodiimide (EDCI, 0.525mmol), 9mg 4-dimethylaminopyridine (DMAP, 0.025mmol) and 43mg benzoic acid (0.35mmol) Mix and stir in 20 mL DMF at room temperature for 10 hours. After the reaction was completed, the reaction solution was poured into 100 mL of water and left to stand for 1 hour, a large amount of precipitates were precipitated, filtered and dried to obtain a light yellow solid crude product. The above crude product was dissolved in 20 mL of ethanol / dioxane (3 / 1) solution, 20 mg of 10% palladium-carbon was added, and the reaction was carried out in a hydrogen atmosphere for 3 hours. After the reaction was completed, filter, the filter cake was washed with ethanol, the filtrate w...

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PUM

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Abstract

The invention belongs to the field of the pharmaceutical chemistry, and relates to quercetin derivatives having a structure represented by formula (I), or analogs thereof, and a use of the quercetin derivatives or the analogs in the inhibition of hepatitis C virus replication. The above compounds or the pharmaceutically acceptable salts thereof can inhibit the replication of hepatitis C viruses in human liver tumor cells, and can be used to prepare medicines for preventing or treating hepatitis C virus related diseases as hepatitis C virus inhibitors, wherein the hepatitis C virus related diseases comprise hepatitis C, and hepatic cirrhosis and hepatic tumors caused by the hepatitis C viruses.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to quercetin derivatives or analogs thereof and applications thereof, in particular to quercetin derivatives and analogs thereof for treating diseases related to hepatitis C virus infection and a preparation method thereof , the salts of the compounds and the medicaments containing the compounds or the salts thereof as active ingredients. Background technique [0002] Hepatitis C virus (HCV) was first discovered in 1989 and is a widespread virus. At present, it is believed that HCV infection can cause chronic hepatitis, liver cirrhosis and hepatocellular carcinoma (HCC). According to the statistics of the World Health Organization in 2010, there are currently about 170 million people infected with HCV in the world, accounting for 3% of the global population, and the number of people infected is still increasing at a rate of 3 to 4 million people every year. [0003] To date there ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30C07D405/12C07D407/12C07D409/12A61K31/352A61K31/4433A61K31/381A61P1/16A61P31/14A61P35/00
Inventor 周璐刘明明叶德泳
Owner FUDAN UNIV
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