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Dicycloglycosides compound, preparation method and application thereof

A technology of bicyclic alcohol glycoside and bicyclic alcohol, which is applied in the directions of sugar derivatives, digestive system, organic chemistry, etc., can solve the problems of low bioavailability and poor water solubility, and achieve the effects of simple preparation method, easy control of conditions and obvious effect.

Inactive Publication Date: 2008-01-16
OCEAN UNIV OF CHINA
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Although bicyclol has a better effect on improving symptoms and lowering serum aminotransferases for chronic hepatitis B and chronic hepatitis C, and also shows a certain antiviral effect in some cases, but it still has some shortcomings. Mainly manifested in poor water solubility and relatively low bioavailability

Method used

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  • Dicycloglycosides compound, preparation method and application thereof
  • Dicycloglycosides compound, preparation method and application thereof
  • Dicycloglycosides compound, preparation method and application thereof

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Embodiment Construction

[0013] The preparation method of bicyclic alcohol glycoside compound of the present invention comprises the following steps:

[0014] 1. the preparation of bicyclic alcohol-glycine ester, its concrete steps are as follows:

[0015]

[0016] Bicyclol Bicyclol-(N-Fmoc)-Glycine Ester Bicyclol-Glycine Ester

[0017] Dissolve bicyclic alcohol (21.2g, 54.4mmol) in 300ml of dry dichloromethane, add Fmoc-protected glycine (18.1g, 65.2mmol), in 1-(3-dimethylaminopropyl)-3-ethyl carbon Under the catalysis of diimine hydrochloride (EDC·HCl, 13.8g, 71.7mmol) and 4-dimethylaminopyridine (DMAP, 1.4g, 10.9mmol), the condensation reaction was carried out under stirring at room temperature, and the reaction progress was detected by TLC, 2.5h After that, the raw material bicyclic alcohol disappears. The reaction solution was washed with water and saturated NaCl aqueous solution successively, and the organic phase was washed with anhydrous NaCl 2 SO 4 After drying and concentration, the r...

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Abstract

Disclosed is a preparation method of a bicyclol glycoside compound, which is characterized in that first bicyclol and glycine protected by Fmoc are condensed under the catalysis of 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride and 4-dimethylamino pyridine, and then protecting group of Fmoc is removed under the effect of acetonitrile diethylamine to obtain intermediate bicyclol-glycine ester which is the condensation of the bicyclol and the glycine. At last, Alpha or Beta glycosyl carboxyl methyl glycoside of glucose, galactose, mannose, allose, altrose, gulose, idose, talose, acetyl-glucosamine or acetyl galactosamine has condensation reaction with the intermediate bicyclol-glycine ester in solvent N-methyl pyrrolidone and under the effect of condensing agent and alkali. The water solubility of the bicyclol can be increased with the invention, and the bioavailability of the bicyclol is improved, which can provide enough raw material and effective compound route for the study of the anti-hepatitis drug. The invention has the advantages that the preparation method is simple and convenient; the condition is easy to control.

Description

technical field [0001] The invention relates to a bicyclic alcohol glycoside compound, a preparation method thereof and an application as an antihepatitis drug. Background technique [0002] Bicyclol is a synthetic anti-hepatitis drug, which has obvious hepatoprotective effect and certain anti-hepatitis virus activity. The research on the mechanism of action of this drug shows that bicyclol protects the liver cell membrane by scavenging free radicals, and protects the liver cell nuclear DNA from Damage and reduce the occurrence of apoptosis, thereby playing a role in liver protection. Its structure can be represented by the following formula: [0003] [0004] European patent EP0353358 discloses its preparation method. During the preparation, the known compound biphenyl diester (the preparation method of biphenyl diester has been disclosed in Japanese Patent JP60209582) is used as raw material, and the dicarboxylic acid derivative is obtained by alkali hydrolysis, and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/26A61K31/7048A61P1/16A61P31/12
CPCY02P20/55
Inventor 李英霞刘运鹏李春霞王鹏
Owner OCEAN UNIV OF CHINA
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