Application of lignin flavanonol in preparation of antiviral drugs

A dihydrogen and drug technology, applied in the directions of antiviral agents, drug combinations, sexually transmitted diseases, etc., can solve the problems that have not been effectively developed, and achieve the effects of convenient source of raw materials, high yield and easy availability of raw materials.

Inactive Publication Date: 2009-10-07
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The silybin compounds have the exact multiple curative effects described above, but their new uses in antiviral aspects including inhibiting herpes simplex virus and inhibiting influenza virus have not been effectively developed, so we have prepared a compound with silybin structure Different new derivatives, that is, introducing dioxane substituents with different parallel positions in the flavone parent B ring, thus forming some novel structures of lignin dihydroflavonols

Method used

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  • Application of lignin flavanonol in preparation of antiviral drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1 : compound of formula (I) (±)-2-[2,3-dihydro-2-(3,5-dimethoxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4benzo Preparation of dioxane-5]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0034] 1.1 Preparation of starting material A-2,4,6-trimethoxymethoxyacetophenone (1):

[0035] Cool the solution of 2.6 g of sodium hydride in 40 ml of DMF in an ice-water bath, add dropwise a mixed solution of 5.6 g of 2,4,6-trihydroxyacetophenone in 60 ml of benzene and 7.0 ml of DMF under nitrogen protection, and cool in an ice-bath 9.0 ml of chloromethyl ether solution was added dropwise, and the mixture was stirred at room temperature for 24 hours. Pour into 100 ml of 10% aqueous sodium hydroxide solution, extract three times with 50 ml of ether, wash with saturated sodium bicarbonate, dry with anhydrous sodium sulfate, filter, concentrate, 40 g of 200-300 mesh silica gel column chromatography, petroleum Elution with ether / ethyl acetate 4:1 gave 7.0 g of starting material...

Embodiment 2

[0048] Example 2 : The cytotoxicity of the compound of formula (I) on Vero cells was determined by MTT method, and the inhibitory effect on HSV-1 was studied by trace cytopathic inhibition (CPE) method.

[0049] 2.1 Experimental purpose

[0050] Using HSV-1-infected Vero cells as a model, anti-HSV drugs were screened, wherein the sample was from the sample of the compound of formula (I) in Example 1.

[0051] 2.2 Materials

[0052] 2.2.1 Viruses and cells

[0053] 2.2.1.1 Virus: HSV-1 is provided by the Laboratory of Traditional Chinese Medicine and Natural Medicine, School of Pharmacy, Zhejiang University;

[0054] 2.2.1.2 Cells: Vero cells were purchased from Shanghai Institute of Cell Biology, Chinese Academy of Sciences.

[0055] 2.3 Reagents

[0056] 2.3.1RPMI 1640 medium: product of Gibco;

[0057] 2.3.2L-Glutamine: AMRESCO products, subpackaged by Shanghai Sangon Bioengineering Technology Service Co., Ltd.;

[0058] 2.3.3MTT: AMRESCO products, subpackaged by Sha...

Embodiment 3

[0081] Example 3 : Inhibitory effect of compound of formula (I) on HSV-2 by microcytopathic inhibition (CPE) method

[0082] 3.1 Experimental purpose

[0083] Using HSV-2-infected Vero cells as a model, anti-HSV drugs were screened, wherein the samples were from the sample of the compound of formula (I) prepared in Example 1.

[0084] 3.2 Materials

[0085] 3.2.1 Viruses and cells

[0086] 3.2.1.1 Virus: HSV-2 is provided by the Institute of Traditional Chinese Medicine and Natural Medicine, School of Pharmacy, Zhejiang University;

[0087] 3.2.1.2 Cells: Vero cells were purchased from Shanghai Institute of Cell Biology, Chinese Academy of Sciences.

[0088] 3.2.2 Reagents

[0089] 3.2.2.1RPMI 1640 medium: product of Gibco;

[0090] 3.2.2.2L-Glutamine: AMRESCO product, subpackaged by Shanghai Sangon Bioengineering Technology Service Co., Ltd.;

[0091] 3.2.2.3MTT: AMRESCO products, subpackaged by Shanghai Sangon Bioengineering Technology Service Co., Ltd.;

[0092] 3....

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PUM

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Abstract

The invention relates to application of lignin flavanonol in preparation of antiviral drugs, particularly, the invention relates to a chemical compound as formula (I), (+-)-2-[2,3-dihydro-2-(3,5-dimethoxy-4-hydroxy phenyl)-3-hydroxymethyl-1,4-benzodioxane-5]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyrone-4-ketone, or use of its medicinal salt used for preparing drugs for repressing herpes simplex virus and / or influenza virus. Pharmacological experiments in vitro shows that the chemical compound (I) can not only repress growth of herpes simplex virus HSV-1, HSV-2 obviously, and repress influenza virus effectively. And so it is expected to be develpoed as anti-infective agents for curing I / II type herpes simplex virus, or develpoed as viral influenza drugs infected by IV A virus.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a lignin dihydroflavonol derivative, namely the compound of formula (I), (±)-2-[2,3-dihydro-2-(3,5 -Dimethoxy-4-hydroxyphenyl)-3-hydroxymethyl-1,4benzodioxane-5]-2,3-dihydro-3,5,7-trihydroxy-4H- Use of 1-benzopyran-4-one or a pharmaceutically acceptable salt thereof for preparing a drug for inhibiting herpes simplex virus or for preparing an anti-influenza virus drug. Background technique [0002] The diameter of herpes simplex virus is about 120-150 microns. The core containing DNA is located in the middle, and it is composed of three concentric structures: envelope, body coat and capsid. The capsid surface is composed of 162 shell particles. 3:3:3 The 2-axis symmetric icosahedron can survive for several months at low temperature, and is inactivated by damp heat at 50°C and drying at 90°C for 30 minutes. Herpes simplex virus can be divid...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/357A61P31/22A61P1/04A61P15/00A61P31/16
Inventor 李校堃冯玉冰黄可新李海波巫秀美赵昱瞿佳郝小江
Owner WENZHOU MEDICAL UNIV
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