2-substituted chromone compound, as well as preparation method and application thereof

A kind of technology of chromone and compound, applied in the field of treatment or prevention of hepatitis B virus infection

Inactive Publication Date: 2012-07-11
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there has been no report about the anti-hepatitis B virus of chromone compounds

Method used

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  • 2-substituted chromone compound, as well as preparation method and application thereof
  • 2-substituted chromone compound, as well as preparation method and application thereof
  • 2-substituted chromone compound, as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 extract compound

[0025] Oval Leaf Flower Anchor ( Halenia epliptica D. Don) (aerial part 5kg) was pulverized and infiltrated with 95% alcohol for 5 days. Concentrate under reduced pressure into alcohol extract, suspend in water and extract with petroleum ether and ethyl acetate respectively. After concentration of the water part, 95% alcohol was added for alcohol precipitation, and the precipitate was filtered off. The clear night was subjected to macroporous resin Diaion HP 20 column chromatography, and the water-ethanol gradient elution (0%-95%) was divided into five parts.

[0026] The part eluted with 20% alcohol was repeatedly eluted by gel Sephadex LH-20 column chromatography (water-methanol gradient elution, 0%-20%) and reverse phase C-18 silica gel column chromatography (30% methanol), get compound 1 (8-Hydroxy-2-methylchromone).

[0027] The part eluted with 95% alcohol was repeatedly eluted by gel Sephadex LH-20 column chromatography (water...

Embodiment 2

[0029] Example 2 extract compound

[0030] Oval Leaf Flower Anchor ( Halenia epliptica D. Don) (aerial part 5kg) was pulverized and infiltrated with 95% alcohol for 5 days. Concentrate under reduced pressure into alcoholic extract, suspend in water and extract with petroleum ether and ethyl acetate respectively. The ethyl acetate part was subjected to silica gel column chromatography (chloroform-acetone 1:0 gradient elution to 0:1).

[0031] Chloroform elution site was obtained by repeated silica gel column chromatography (chloroform elution) to obtain the compound 2 (8-methoxy-2-methylchromanone).

[0032] Chloroform-acetone (5:1) elution site was subjected to repeated silica gel column chromatography (chloroform-acetone 6:1 elution) to obtain the compound 1( 8-hydroxy-2-methylchromanone).

Embodiment 3

[0033] Example 3 In vitro anti-HBV activity test

[0034] Apply Hep G 2 2.2.15 Cell lines, 10'10 per well 5 Cells were inoculated in a 96-well plate, the medium was DMEM, the growth medium contained 10% fetal bovine serum, 100 units / mL penicillin, 100 μg / mL streptomycin, 2 mmol / L L-glutamine, 5% CO 2 in the incubator37 o C culture, the compound medicine of the present invention is dissolved in dimethyl sulfoxide, is diluted to 100, 50 and 25 μ g / mL respectively, after cell culture 48 hours, changes into the culture medium containing medicine, continues to cultivate 9 days (changing medium every 2 days) Once), the supernatant was collected to detect HBsAg and HBeAg by ELISA method. Under the same conditions, the culture supernatant without drugs was used as a control, and lamivudine (3TC) was used as a positive control. The cytotoxicity of drugs was determined by MTT method. The results confirmed that 8-hydroxy-2-methylchromanone ( 1 ) and 8-methoxy-2-methyl ( 2 ) has...

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PUM

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Abstract

The invention belongs to the field of medicaments, and relates to a 2-substituted chromone compound, as well as a preparation method and application thereof. In-vitro anti-HBV (hepatitis b virus) activity test results of the 2-substituted chromone compound prove that: the 2-substituted chromone compound has remarkable anti-HBV effect, low effective concentration and low cytotoxicity. A medicinal composition can be further prepared from the 2-substituted chromone compound to be used for treating or preventing infection of hepatitis b virus, and particularly for inhibiting replication of surface antigen and e-antigen of the hepatitis b virus. The medicinal composition provided by the invention can be given nasally, orally, transdermally, parenterally, or by venous or intramuscular injection.

Description

technical field [0001] The invention belongs to the field of medicaments, and relates to 2-substituted chromone compounds and their preparation method and application, especially the application for treating or preventing hepatitis B virus infection. Background technique [0002] The prior art discloses that hepatitis B is a chronic infectious disease with high incidence and great harm caused by hepatitis B virus (HBV). According to reports, there are currently at least 350 million people infected with hepatitis B virus (HBV) in the world, and the HBsAg carrier rate in the Chinese population is 9.75%, exceeding 100 million people. Among HBV-infected patients, about 25% eventually died of severe chronic liver disease, liver cirrhosis and primary liver cancer. About 600,000 patients die from liver disease every year in our country, and 1 / 2 of them are liver cancer, which causes huge loss of talents and economy to our country. [0003] Due to the complexity of hepatitis B, wh...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22A61K31/353A61P31/20
Inventor 俞培忠孙雨伟章瑶
Owner FUDAN UNIV
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