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Application of benzo-phenylpropanoids in preparing drug for treating viral hepatitis B

A technology of benzophenanil and its application, which is applied in the application field of benzophenanil for preparing a drug for the treatment of viral hepatitis B, and can solve the problems such as the anti-HBV activity of benzophenazone compounds that are not reported.

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] 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, in which there is no relevant record of any phenylpropanoid compounds having anti-HBV activity, especially phenylpropanoids and their derivatives containing aromatic aldehyde groups with the structure shown in formula (1), domestic hardly anyone involved

Method used

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  • Application of benzo-phenylpropanoids in preparing drug for treating viral hepatitis B
  • Application of benzo-phenylpropanoids in preparing drug for treating viral hepatitis B
  • Application of benzo-phenylpropanoids in preparing drug for treating viral hepatitis B

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Compound (±)-2,3-trans-3-(3,4-Dimethoxyphenyl-2-hydroxymethyl-2,3-dihydrobenzo[b][1,4]dioxane Preparation of cyclo-6-yl-formaldehyde

[0027] Instruments and reagents:

[0028] UV spectrum was measured with Shimadzu UV-240 UV spectrophotometer; proton nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is the internal standard); ESI-MS is measured by BrukerEsquire 3000+ mass spectrometer, column chromatography uses silica gel (100-200, 200-300 and 300-400 mesh) and thin layer chromatography silica gel GF254 (10-40 mesh) are produced by Qingdao Ocean Chemical Plant; all reagents used are analytical pure, thin layer preparative chromatography (PTLC) ) Use Merck's aluminum foil silica gel plate; Sephadex LH-20 for column chromatography uses the product of Amersham Pharmacia Biotech AB in Sweden; reverse-phase silica gel RP-18 uses the Chromatorex pr...

Embodiment 2

[0034] Example 2: Compound (±)-2,3-trans-3-(3-methoxy-4-hydroxyphenyl)-2-hydroxymethyl-2,3-dihydrobenzo[b][1,4] two Preparation of oxane-6-yl-formaldehyde

[0035] Apparatus and reagents: the same as in Example 1.

[0036] 2.1 Preparation method 1 (direct oxidation coupling method under silver salt catalysis):

[0037] In a dry 500 ml three-necked flask, add 0.38 g of 3,4-dihydroxybenzaldehyde and 0.52 g of coniferyl alcohol, and add 80 ml of anhydrous benzene and 20 ml of anhydrous acetone under argon protection. Stir at 60°C for 20 minutes, then add 0.765 g of silver carbonate and stir vigorously for 7 hours. The mixture was filtered, the filtrate was concentrated under reduced pressure, and the sample was mixed with silica gel, followed by 16 g of 200-300 mesh silica gel column chromatography, and repeated elution with petroleum ether: ethyl acetate (3:1) to obtain 0.328 g of a yellow solid. The yield was 38. %. R f (Chloroform / methanol=25:1): 0.32; proton nuclear magnetic re...

Embodiment 3

[0041] Example 3: (±)-2,3-trans-3-(3,4-Dimethoxyphenyl)2-hydroxymethyl-2,3-dihydrobenzo[b][1,4]dioxane -6-yl-formaldehyde inhibits the replication of hepatitis B virus deoxyribonucleic acid (HBV DNA) secreted by HepG2.2.15 cells

[0042] 3.1 Cell culture:

[0043] HepG2.2.15 cells were cultured in DMEM medium containing 10% inactivated fetal bovine serum, 100U / ml penicillin and 100U / ml streptomycin, 100μg / ml G418, and placed at 37°C, 5% CO 2 , Cultivate in an incubator with 100% relative humidity.

[0044] 3.2 Determination of compound (±)-2,3-trans-3-(3,4-dimethoxyphenyl)2-hydroxymethyl-2,3-dihydrobenzo[b][1, using MTT method 4] The inhibitory effect of dioxane 6-yl-formaldehyde on the growth of HepG2.2.15 cells:

[0045] Take HepG2.2.15 cells in logarithmic growth phase and dilute the cells to 1×10 with medium 5 Pcs / ml, seeded on 96-well cell culture plate, 100 microliters per well, at 37℃, 5% CO 2 After culturing in a 100% relative humidity incubator for 24 hours, add the compoun...

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Abstract

The invention relates to an application of benzo-phenylpropanoids in preparing drugs for treating viral hepatitis B, in particular to two benzo-phenylpropanoids or application of pharmaceutically acceptable salt thereof in preparing drugs for inhibiting the replication of hepatitis B virus desoxyribonucleic acid (HBV DNA) and treating hepatitis B virus infection diseases. The two benzo-phenylpropanoids definitely inhibit the activity of the HBV DNA, have the replication inhibition activity on the HBV DNA at high dose (100 microgrammes / milliliter) of 1.3-2.2 times higher than the inhibition activity at the highest concentration (10000 units / milliliter) of an alpha-interferon and belong to an efficient non-nucleoside natural product inhibiting the hepatitis B viruses; pharmacodynamics results show the application of the benzo-phenylpropanoids or the pharmaceutically acceptable salt thereof capable of preparing the drugs for inhibiting the replication of the HBV DNA and treating the hepatitis B virus infection diseases in anticipation.

Description

Technical field [0001] The present invention relates to the technical field of medicine. Specifically, the present invention relates to two phenylpropanoids represented by formula (1) or their pharmaceutically acceptable salts for preparing and inhibiting hepatitis B virus deoxyribonucleic acid HBV DNA replication and treatment The use of hepatitis B drugs. The diphenylpropanine has the exact inhibitory activity of HBV DNA, and its replication inhibitory activity on HBV DNA at high doses (100 μg / ml) is α-interferon at the highest concentration of 10,000 The inhibitory activity at a unit / ml concentration is 1.3 to 2.2 times, and one of them exceeds the inhibitory activity of the positive control drug lamivudine on HBV DNA at the same concentration. It is an extremely powerful non-nucleoside natural product for inhibiting hepatitis B virus. The pharmacodynamic results show that the phenophenone or its pharmaceutically acceptable salt can be expected to be used in the preparation o...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/20
Inventor 李凤贤孙莲莉吴俊珠杨雷香廖晓辉巫秀美赵昱郝小江
Owner DALI UNIV
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