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Anti-hepatitis C virus compound, preparation method and application thereof

A compound and composition technology, applied in the field of medicinal chemistry and pharmacotherapeutics, can solve the problems of poor solubility, affecting bioavailability and drug efficacy, etc.

Active Publication Date: 2014-09-24
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, compounds with the general formula shown in formula 21 tend to have poor solubility, which affects their bioavailability and efficacy in vivo

Method used

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  • Anti-hepatitis C virus compound, preparation method and application thereof
  • Anti-hepatitis C virus compound, preparation method and application thereof
  • Anti-hepatitis C virus compound, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0124] Synthesis of 2,6-dibenzyloxybenzonitrile (compound shown in formula 4)

[0125] Dissolve 0.5 g of sodium benzyl alcohol in 10 ml of dimethyl sulfoxide, and add 2,6-difluorobenzonitrile under stirring. After rapidly raising the temperature to 115°C, stirring was continued for 8 hours. After cooling to room temperature, 100 ml of ice water was poured into the reaction liquid, and the stirring was continued for 30 minutes. A large amount of solid precipitated out, which was filtered by suction, washed with water, and dried to obtain 2,6-dibenzyloxybenzonitrile as a white solid.

[0126] 1 H-NMR (400Mz, DMSO-d6) δ: 5.19 (4H, s), 6.60 (2H, d), 7.30-7.35 (3H, m), 7.38 (4H, t), 7.45 (4H, d).

Embodiment 2

[0128] Synthesis of 2,6-dibenzyloxybenzamide (compound shown in formula 5)

[0129] Dissolve 0.4 gram of 2,6-dibenzyloxybenzonitrile (compound shown in formula 4) in 7 milliliters of benzyl alcohol, and add 0.6 gram of potassium hydroxide, 0.6 gram of n-tetrabutylammonium bromide and 0.1 milliliter of water, 140 Stir at °C for 24 hours. After the reaction, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 2,6-dibenzyloxybenzamide as a white solid.

[0130] 1 H-NMR (400Mz, DMSO-d6) δ: 5.15 (4H, s), 6.60 (2H, d), 7.18-7.48 (12H, m), EI-MS m / z333.2 (M + ), 91.1 (100%).

Embodiment 3

[0132] Synthesis of 1-(fluoren-9-yl)-3-(2,6-dibenzyloxybenzoyl)urea (compound represented by formula 8)

[0133] Dissolve 0.5 g of triphosgene in 3 ml of 1,2-dichloroethane, and stir in an ice bath until dissolved. Dissolve 0.25 g of 9-fluorenamine in 10 ml of 1,2-dichloroethane, and slowly add it dropwise to the reaction solution containing triphosgene. The reaction solution is white and turbid. Continue to stir in the ice bath for 0.5 hours and then heat up to 25 °C for 1 hour, and then heated to reflux until the reaction solution was colorless and transparent, and 1 ml of triethylamine was added to the reaction solution to continue the reflux reaction for 0.5 hours. The solvent was evaporated under reduced pressure, and 10 ml of toluene was added for filtration. 0.35 g of 2,6-dibenzyloxybenzamide (compound represented by formula 5) was added to the filtrate, and refluxed for 12 hours. The solvent was distilled off under reduced pressure, and the residue was purified by si...

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Abstract

The invention provides an anti-hepatitis C virus compound, a preparation method and an application thereof. The compound is the compound shown in a formula I or a stereisomer, a geometric isomer and a tautomer of the compound shown in the formula I, wherein R1 and R2 are respectively and independently selected from hydrogen, formyl group, benzoyl group and C1-C3 straight chain or branched chain alkyl group, and R1 and R2 can not be hydrogen at the same time. The compound has good lipid solubility and physical and chemical property, and bioavailability and effect in-vivo can be obviously increased.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and drug therapeutics, in particular, the invention relates to an anti-hepatitis C virus compound and its preparation method and application. Background technique [0002] Hepatitis C (Hepatitis C) is a group of systemic infectious diseases mainly caused by liver damage caused by hepatitis C virus (HCV). HCV is a threat to humans not only because of its high prevalence, but also because of the potentially serious complications of persistent HCV infection. This chronic disease can lead to advanced liver diseases such as cirrhosis and liver cancer. In recent years, the rapid progress of HCV biology has led to a breakthrough understanding of HCV infection and replication, which has had an important impact on the research and development of anti-HCV drugs. Anti-HCV research by interfering with host cell proteins related to HCV replication has attracted widespread attention and many breakthroughs h...

Claims

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Application Information

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IPC IPC(8): C07C275/54C07C273/18A61K31/17A61P31/14
Inventor 刘磊张林琦蒋华良李剑闫文仲卿杰
Owner TSINGHUA UNIV
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