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Use of lignanoid containing benzyloxy flavones in preparation of drugs for treating viral hepatitis B

A dihydroflavonol lignan and application technology, which is applied in the field of medicine, can solve the problems that new applications have not been effectively developed, and achieve the effects of large-scale production, simple and easy preparation method, and easy-to-obtain raw material sources

Inactive Publication Date: 2010-09-15
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] Although flavonoid lignans represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on antiviral treatment. Flavonoids are especially effective in treating DNA virus infections Its new uses for anti-hepatitis B virus (including inhibition of HBsAg or HBeAg, inhibition of HBV DNA replication) have not been effectively developed

Method used

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  • Use of lignanoid containing benzyloxy flavones in preparation of drugs for treating viral hepatitis B
  • Use of lignanoid containing benzyloxy flavones in preparation of drugs for treating viral hepatitis B
  • Use of lignanoid containing benzyloxy flavones in preparation of drugs for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Formula (1) (±)-2-[2,3-dihydro-2-(3-benzyloxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4 benzodioxane- 5] Preparation of -2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0034] Instruments and reagents:

[0035] The ultraviolet spectrum was measured with a Shimadzu UV-240 ultraviolet spectrophotometer; the hydrogen nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA type superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is the internal standard); (100-200, 200-300 and 300-400 mesh) and silica gel GF254 (10-40 mesh) for thin layer chromatography are all produced by Qingdao Ocean Chemical Factory; all reagents used are analytically pure, and the boiling range of petroleum ether is 60 -90°C; thin-layer preparative chromatography (PTLC) uses aluminum foil silica gel plates from Merck; column chromatography uses dextran gel Sephadex LH-20 from Amersham Pharmacia Biotech AB in Sweden; reverse-ph...

Embodiment 2

[0054] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0055] 2.1 Cell culture:

[0056] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100 U / ml penicillin and 100 U / ml streptomycin, 100 μg / ml G418 at 37°C, 5% CO 2 , cultured in an incubator with 100% relative humidity.

[0057] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0058] Take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1×10 with medium 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2 After 24 hours in an incubator with 100% relative humidity, add compound (1) diluted with medium, the concentration is 1000 μg / ml, 200 μg / ml, 40 μg / ml and 8 μg / ml, 200 μg / ml in each well microliter, each concentration was set up in triplicate, placed at 37°C, 5% CO 2 , cultivated in an ...

Embodiment 3

[0067] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0068]3.1 Cell culture: the method is the same as in Example 2.

[0069] 3.2 Determination of the inhibitory effect of the compound of formula (1) on the growth of HepG2.2.15 cells by MTT method: the method is the same as in Example 2.

[0070] 3.3 Determination of the inhibitory effect of the compound on hepatitis B e antigen (HBeAg): take the HepG2.2.15 cells in the logarithmic growth phase, and dilute the cells to 1 × 10 with the medium 5 / ml, seeded in 96-well cell culture plate, 100ml per well, at 37°C, 5% CO 2 After culturing in an incubator with 100% relative humidity for 24 hours, add samples diluted with culture medium at concentrations of 20 μg / ml, 4 μg / ml and 0.8 μg / ml, 200 μl per well, and set three concentrations for each Multiple wells were placed at 37°C, 5% CO 2 , cultivated in an incubator with 100% relative humidity, change the culture medi...

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Abstract

The invention relates to a use of lignanoid containing benzyloxy flavones in the preparation of drugs for treating viral hepatitis B, in particular to the use of a compound as shown in formula (1) or pharmaceutical salts thereof in the preparation of the drugs for eliminating hepatitis B virus surface antigen and hepatitis B e antigen and the drugs for suppressing HBV DNA replication, and the strength of eliminating HBsAg of flavonol lignanoid under the concentration of 20 mu g / ml is 50.8%, which is 3.2 times of the corresponding activity of a positive control drug; the activity of eliminating the HBeAg under the same concentration is equivalent to 10000 units / ml of alpha-interferon; simultaneously, the flavonol lignanoid shows nearly 60% of suppression rate to HBV DNA under the concentration, which is 1.6 times of the corresponding suppression rate of the alpha-interferon. The results show that the lignanoid containing the flavones or the pharmaceutical salts thereof are expected to be used for preparing the non-nucleoside drugs for eliminating the HBsAg and the HBeAg, suppressing the HBV DNA replication and treating hepatitis B virus infection diseases.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular, the invention relates to a dihydroflavonol lignan compound of B-ring dioxane or a pharmaceutically acceptable salt thereof for the preparation of reducing hepatitis B virus surface antigen HBsAg and hepatitis B e antigen Use of HBeAg, inhibiting HBV DNA replication, and treating hepatitis B virus infection diseases. The flavonoid lignans have significant HBsAg and HBeAg inhibitory activity, and its HBsAg removal intensity is 50.8% at a concentration of 20 micrograms / ml, which is 3.2 times the corresponding activity of the positive control drug (10000 units / ml of α-interferon); At the same concentration, its activity of removing HBeAg is equivalent to that of 10000 units / ml of α-interferon; at the same time, at this concentration, it shows an inhibition rate of nearly 60% for HBV DNA, which is 1.6% of the corresponding inhibition rate of α-interferon. times. The above pharmacodynam...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 白丽娄旭刘正文李海波白骅巫秀美赵昱谭仁祥
Owner DALI UNIV
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