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Application of diallyl propyl flavonolignan in preparation of medicament for curing hepatitis B

A flavonoid lignan and allyl group substitution technology is applied in the direction of drug combinations, medical preparations containing active ingredients, and pharmaceutical formulas. It can solve the problems that new uses have not been effectively developed, and achieve large-scale production. Large-scale production, less pollution effect

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

[0014] Although the flavonoid lignans represented by silibinin have the above-mentioned antioxidant effects, there are relatively few literatures on their antiviral treatment. The flavonoid lignans treat DNA virus infection especially Its new application for anti-hepatitis B virus (including inhibition of hepatitis B e antigen HBeAg or inhibition of HBV DNA replication) has not been effectively developed, so the active compound in the field of anti-hepatitis B virus, namely flavonoid lignans, is sought from flavonoid lignans. Structural engineering for anti-DNA viroid activity is a new field

Method used

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  • Application of diallyl propyl flavonolignan in preparation of medicament for curing hepatitis B
  • Application of diallyl propyl flavonolignan in preparation of medicament for curing hepatitis B
  • Application of diallyl propyl flavonolignan in preparation of medicament for curing hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Formula (1) compound 2,3-dihydro-2-[2,3-dihydro-3-(4-allyloxy-3-methoxyphenyl)-2-hydroxymethyl-1, Preparation of 4-benzodioxane-6-]-7-(allyloxy)-3,5-dihydroxy-4H-1-benzopyran-4-one

[0026] The present invention has prepared the flavonoid lignan compound shown in formula (1) by a de novo synthesis method. In addition to this method, it can also be used to directly carry out the final oxidative coupling reaction with commercially available silibinin and allyl bromide. The compound of formula (1) is generated in one step. The instruments and reagents used include:

[0027] 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 laye...

Embodiment 2

[0044] Example 2: Inhibitory effect of compound of formula (1) on hepatitis B e antigen (HBeAg) secreted by HepG2.2.15 cells

[0045] 2.1 Cell culture:

[0046] 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.

[0047] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0048] 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 i...

Embodiment 3

[0055] Example 3: Inhibition of the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by the compound of formula (1) to HepG2.2.15 cells

[0056] 3.1 Cell culture: the method is the same as in Example 2.

[0057] 3.2 The inhibitory effect of the flavonoid lignan compound represented by formula (1) on the growth of HepG2.2.15 cells was determined by MTT method: the method is the same as that in Example 2.

[0058] 3.3 The flavonoid lignan compounds shown in the assay formula (1) inhibit the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA): get the HepG2.2.15 cells in the logarithmic growth phase, and use the culture medium to dilute the cells to 1 ×10 5 cells / ml, seeded in 96-well cell culture plate, 100 μl per well, at 37°C, 5% CO 2After cultivating in an incubator with 100% relative humidity for 24 hours, add the flavonoid lignan compound shown in the formula (1) diluted with the medium, the concentration is respectively 5 microgram...

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Abstract

The invention relates to application of diallyl propyl flavonolignan in preparation a medicament for curing hepatitis B, in particular to application of a flavonolignan or pharmaceutically acceptable salts thereof in preparation of the medicament for curing the hepatitis B by clearing hepatitis B e-antigen and inhibiting HBV DNA replication. The flavonolignan has hepatitis B virus e-antigen (HBeAg) inhibiting activities, and has the inhibition strength higher than a positive control first-line medicament, namely lamivudine and alpha-interferon, at a low concentration of 20 mu g / ml; simultaneously, at the concentration of 5 mu g / ml, the compound has an inhibition rate of the HBV DNA of over 70 percent; and therefore, the flavonolignan can be expected for preparing the medicament for curing the hepatitis B virus infection diseases by clearing the hepatitis B e-antigen and inhibiting the HBV DNA replication.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to the use of diallyl-substituted flavonoid lignans represented by formula (1) or pharmaceutically acceptable salts thereof in the preparation of scavenging hepatitis B e antigen and inhibiting hepatitis B virus deoxygenation Ribonucleic acid HBV DNA replication, the use of drugs for the treatment of hepatitis B virus, the flavonoid lignans have been found to have a strong inhibitory effect on the activity of hepatitis B e antigen through pharmacodynamic tests, and its inhibitory strength is far lower at a low concentration of 20 μg / ml It is higher than the positive control first-line drugs lamivudine and α-interferon, and at the very low concentration of 5 μg / ml, the compound can still show an inhibition rate of more than 70% on HBV DNA, which is an extremely rare inhibition of hepatitis B Virus active compounds can be expected to be developed ...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20A61P1/16C07D407/04
Inventor 谭云波郑威吕小满李海波金一巫秀美赵昱曾苏
Owner DALI UNIV
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