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Application of B-ring ethyoxyl flavanonol in preparing medicaments for treating hepatitis B viruses

A dihydroflavonol and ethoxy technology, applied in the field of medicine, can solve the problems of no reported anti-HBV activity, etc., and achieve the effects of clear industrialization prospects, large-scale production of energy saving and emission reduction, and convenient synthesis

Inactive Publication Date: 2012-05-23
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Zuo Guoying et al. (Zuo Guoying, Liu Shuling, Xu Guili, World Chinese Journal of Digestion, 2006, Vol. 14, No. 13, pp. 1241-1246) reviewed the research progress of the anti-HBV activity of medicinal plant ingredients in vitro in the past 20 years. Natural products, flavonoids and flavonols (such as quercetin) have also been reported to have anti-HBV activity in vitro, but there is no report that compounds with dihydroflavonols have anti-HBV activity, especially those substituted by the B ring Dihydroflavonol compounds, so the inventors carried out structural modification and anti-HBV activity research on them that have not been paid attention to before

Method used

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  • Application of B-ring ethyoxyl flavanonol in preparing medicaments for treating hepatitis B viruses
  • Application of B-ring ethyoxyl flavanonol in preparing medicaments for treating hepatitis B viruses
  • Application of B-ring ethyoxyl flavanonol in preparing medicaments for treating hepatitis B viruses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Formula (1) compound (±)-2,3-trans-(3-ethoxy 4,5-dihydroxyphenyl)--3,5,7-trihydroxy-4H-1-benzopyran- Preparation of 4-keto

[0026] 1.1 Instruments and reagents:

[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-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-phase silica gel RP-18 adopts the Chromatorex product of Fuji Silysia Ch...

Embodiment 2

[0037] Example 2: Inhibitory Effect of Compound (1) on Hepatitis B Surface Antigen (HBsAg) Secreted by HepG2.2.15 Cells

[0038] 2.1 Cell culture:

[0039] 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.

[0040] 2.2 The inhibitory effect of the compound of formula (1) on HepG2.2.15 cell growth was measured by MTT method:

[0041] 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

[0051] Example 3: Inhibitory Effect of Compound (1) on Hepatitis B e Antigen (HBeAg) Secreted by HepG2.2.15 Cells

[0052] 3.1 Cell culture: the method is the same as in Example 2.

[0053] 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.

[0054] 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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Abstract

The invention relates to application of B-ring ethyoxyl flavanonol in preparing medicaments for treating hepatitis B viruses, in particular to application of a compound as shown in a formula (1) or a medicinal salt thereof in preparing medicaments for clearing away hepatitis B virus surface antigens (HBsAg) and hepatitis B e-antigen (HBeAg) and medicaments for inhibiting the duplication of hepatitis B virus desoxyribonucleic acid (HBV DNA). The compound or the medicinal salt thereof has extremely obvious activity on inhibiting the HBsAg and the HBeAg, and in the presence of a concentration of20 microgram / milliliter, the intensities for clearing away the HBsAg and the HBeAg of the compound or the medicinal salt thereof are respectively 99.8 percent and 48.5 percent and are 6.2 times and 2.7 times of that of alpha-interferon which is a positive control medicament. More importantly, in the presence of the concentration, the inhibition ratio of the compound or the medicinal salt thereof to the HBV DNA is 64.7 percent, and the activity is 1.7 times of that of the alpha-interferon. Accordingly, the flavone lignan or the medicinal salt thereof can be expected to be used for preparing non-nucleoside medicaments for treating infectious diseases of the hepatitis B viruses.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, the present invention relates to a kind of B ring ethoxy substituted dihydroflavonol or its pharmaceutically acceptable salt is used for preparing and reducing hepatitis B virus surface antigen HBsAg and hepatitis B e antigen HBeAg, inhibiting HBV DNA Use of medicines for replicating or treating hepatitis B virus infection. This flavonoid lignan has definite activity of inhibiting HBsAg and HBeAg, and its intensity of removing HBsAg and HBeAg is respectively 99.8% and 48.5% under the concentration of 20 micrograms / milliliter, is positive contrast drug (10000 unit / milliliter α-interference 6.2 times and 2.7 times that of interferon; more importantly: at this concentration, it shows a 64.7% inhibition rate to HBV DNA, and its activity is 1.7 times that of interferon. The above pharmacodynamic results show that the B ring ethoxy substituted dihydroflavonol or its pharmaceutical...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/353A61P1/16A61P31/20C07D311/32
Inventor 刘光明董南李树楠汪峰岳建民巫秀美赵昱郝小江
Owner DALI UNIV
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