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

A technology of benzophenanil and viral hepatitis, which is applied in the application field of benzophenanil for preparing a drug for treating viral hepatitis B, and can solve the problems such as no report on the anti-HBV activity of benzophenanate compounds

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

[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]dioxahexa Preparation of cyclo-6-yl-carbaldehyde

[0027] Instruments and reagents:

[0028] 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 Si...

Embodiment 2

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

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

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

[0037] In a dry 500 ml three-necked flask, 0.38 g of 3,4-dihydroxybenzaldehyde and 0.52 g of coniferyl alcohol were added, and 80 ml of anhydrous benzene and 20 ml of anhydrous acetone were added 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 after adding silica gel to mix the sample, 16 grams of 200-300 mesh silica gel column chromatography was used for repeated elution with petroleum ether: ethyl acetate (3: 1) to obtain 0.328 grams of a yellow solid with a yield of 38 %. R f (chloroform / methanol=25:1)...

Embodiment 3

[0041] Example 3: (±)-2,3-trans-3-(3,4-dimethoxyphenyl)2-hydroxymethyl-2,3-dihydrobenzo[b][1,4]dioxane Inhibitory effect of -6-yl-formaldehyde on 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, 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.

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

[0045] 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 (±)-2,3-...

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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 shown in formula (1) or its pharmaceutically acceptable salt are used for preparing and inhibiting hepatitis B virus deoxyribonucleic acid HBV DNA replication, treatment The purposes of hepatitis B medicine, this diphenylpropanoid has definite inhibition HBV DNA activity, and its replication inhibitory activity to HBV DNA when high dose (100 micrograms / milliliter) is alpha-interferon at highest concentration 10000 1.3 to 2.2 times the inhibitory activity of the unit / ml concentration, and one of them exceeds the inhibitory activity of the positive control drug lamivudine to HBV DNA at the same concentration. The pharmacodynamic results show that the phenylpropanoids or their pharmaceutically acceptable salts can be expected to be used in the preparation of drugs for inhibiting HBV DNA replication and treating hepatitis B vi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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