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Use of acetamide dehydrogenation silibinin as medicament for treating viral hepatitis B

A technology for dehydrosilibinin and acetamide, applied in the field of medicine, can solve the problem that new uses have not been effectively developed, and achieve the effects of convenient source of raw materials, large-scale production of energy saving and emission reduction, and convenient synthesis

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

[0015] 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 application for anti-hepatitis B virus (including inhibition of HBsAg or HBeAg, inhibition of HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus is found from flavonoid lignans, that is, the structure of flavonoid lignans Engineering to have anti-DNA viroid activity is a new field

Method used

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  • Use of acetamide dehydrogenation silibinin as medicament for treating viral hepatitis B
  • Use of acetamide dehydrogenation silibinin as medicament for treating viral hepatitis B
  • Use of acetamide dehydrogenation silibinin as medicament for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Formula (1) compound N, N-diethyl-2-{2-[3-(3-methoxy-4-hydroxyl-phenyl)-2-hydroxymethyl-2,3-dihydro-benzene Preparation of [1,4]dioxane-6-yl]-3,5-dihydroxy-4-oxo-4H-benzopyran-7-yloxy}-acetamide

[0028] 1.1 Instruments and reagents:

[0029] 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 produced by Qingdao Ocean Chemical Factory; all reagents used are analytically pure, thin-layer preparative chromatography (PTLC ) uses the aluminum foil silica gel plate of Merck Company; Sephadex LH-20 used for column chromatography adopts the product of Amersham Pharmacia Biotech AB Company of Sweden; Reversed-...

Embodiment 2

[0033] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0034] 2.1 Cell culture:

[0035] 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.

[0036] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0037] 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

[0047] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0048] 3.1 Cell culture: the method is the same as in Example 2.

[0049] 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.

[0050] 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 med...

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PUM

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Abstract

The invention relates to the use of acetamide dehydrogenation silibinin as a medicament for treating viral hepatitis B, in particular to the use of dehydrogenation silibinin esters flavonoid lignanoid replaced by A ring methoxy formyl amine or pharmaceutically acceptable salt as the medicament for eliminating HBsAg (hepatitis B surface antigen) and HBeAg (hepatitis Be antigen) and restraining copy of HBV DNA. The cetamide dehydrogenation silibinin can obviously restrain the HBsAg and HBeAg activity, and the strengths for eliminating the HBsAg and HBeAg are 90.5% and 63.6% at the concentration of 20 microgramme / milliter and are 5.6 times and 3.8 times more than positive contrast medicament alpha-interferon. Meanwhile, the restraining rate to the HBV DNA is 90.4% at the concentration, is 12% higher than lamivudine, and is 2.4 times more than a- interferon. Therefore, the flavonoid lignanoid or the pharmaceutically acceptable salt can be expected for treating hepatitis B virus infection as the non-nucleoside medicament.

Description

technical field [0001] The invention relates to the field of medical technology, in particular, the invention relates to a dehydrosilibinin ester flavonoid lignan or a pharmaceutically acceptable salt thereof which is substituted by dicarbamoylmethoxy on the A ring and is used for the preparation of Application of the hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, the medicine for inhibiting HBV DNA replication, and treating hepatitis B virus infection diseases. This flavonoid lignan has a very significant activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 90.5% and 63.6% at a concentration of 20 micrograms per milliliter, surpassing positive control drugs (α of 10000 units / ml) respectively. - interferon) 5.6 times and 3.8 times; what is more noteworthy is that it shows 90.4% inhibition rate to HBV DNA at this concentration, 12% higher than lamivudine, and 2.4 times higher than alpha-interferon . Th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 楼宜嘉周琪彭芳胡明辉田景奎巫秀美赵昱郝小江
Owner DALI UNIV
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