Application of 4-cinnamoyl chloride silybin in preparing medicaments for treating viral hepatitis B

A technology of silibinin ester and chlorine meat, applied in] The present invention relates to the field of medical technology, and can solve the problems such as new uses that have not been effectively developed, and achieve the effects of convenient and easy-to-obtain raw material sources, little pollution, 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

[0010] 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 (especially inhibiting HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus is searched from flavonoid lignans, that is, the structural modification of flavonoid lignans makes it have Anti-DNA viroid activity is a brand-new field, and it is an unprecedented challenge to discover lead compounds that inhibit HBV DNA replication

Method used

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  • Application of 4-cinnamoyl chloride silybin in preparing medicaments for treating viral hepatitis B
  • Application of 4-cinnamoyl chloride silybin in preparing medicaments for treating viral hepatitis B
  • Application of 4-cinnamoyl chloride silybin in preparing medicaments for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Compound of formula (1) [3-(4-hydroxy-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxy-4-oxo-1-benzo Preparation of pyran-2)-2,3-dihydro-1,4-benzodioxane-2-]methyl ester

[0023] 1.1 Instruments and reagents:

[0024] 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; rev...

Embodiment 2

[0029] Example 2: Inhibition of the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by the compound of formula (1) to HepG2.2.15 cells

[0030] 2.1 Cell culture:

[0031] 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.

[0032] 2.2 The inhibitory effect of compound (1) on the growth of HepG2.2.15 cells was determined by MTT method:

[0033] 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 cultivating in an incubator with 100% relative humidity for 24 hours, add compound (1) diluted with medium, the concentration is 1000, 200, 40, 8 micrograms / ml respectively, 200 microliters per well, and three concentrations are set for each Dupl...

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Abstract

The invention relates to application of 4-cinnamoyl chloride silybin in preparing medicaments for treating viral hepatitis B, in particular to application of 4-cinnamoyl chloride substituted silybin ester type flavonolignan or a pharmaceutically acceptable salt thereof in preparing medicaments for suppressing HBV (Hepatitis B Virus) DNA replication and treating HBV infection diseases. The flavonolignan has definite activity on suppressing the HBV DNA, and the suppression activity on the replication of the HBV DNA under a high dose approaches that of alpha-interferon under a highest concentration of 10,000 units / milliliter, thus the flavonolignan belongs to effective non-nucleoside natural products for resisting the HBV. The pharmacodynamical results indicate that the flavonolignan or the pharmaceutically acceptable salt thereof can be expected to be used for preparing the medicaments for suppressing the HBV DNA replication and treating the HBV infection diseases.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, the present invention relates to a 4-chlorocinnamoyl substituted silibinin ester type flavonolignan represented by formula (1) or a pharmaceutically acceptable salt thereof for the preparation of Hepatitis virus deoxyribonucleic acid HBV DNA replication, the purposes of treating hepatitis B virus medicine, this flavonoid lignan has definite inhibition hepatitis B virus HBV DNA activity, it is to hepatitis B virus HBV DNA when high dose (100 micrograms / milliliter) The replication inhibitory activity is close to the inhibitory activity of α-interferon at the highest concentration of 10000 units / ml, and it is an effective non-nucleoside natural product for inhibiting hepatitis B virus. The above pharmacodynamic results show that the flavonoid lignan or its medicinal properties The salt can be expected to be used in the preparation of medicines for inhibiting HBV DNA replication ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/20A61P1/16
Inventor 刘光明徐昭君李春艳王彦广罗尔夫·希尔根菲尔德巫秀美赵昱曾苏
Owner DALI UNIV
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