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Application of lignin flavanonol in preparation of antiviral drugs

A technology of dihydrogen and drugs, which is applied in the direction of antiviral agents, drug combinations, and pharmaceutical formulations, can solve the problems of not being effectively developed, and achieve the effects of inhibiting herpes simplex virus, high yield, and conducive to industrialization

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

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Problems solved by technology

[0007] The silybin compounds have the above-mentioned definite multiple curative effects, but their new application in antiviral aspects, especially the inhibition of herpes simplex virus, has not been effectively developed, so the present invention selects and prepares the The different new derivatives, that is, the introduction of dioxane substituents with different parallel positions in the flavone B ring, thus forming a new class of lignin dihydroflavonol compounds, and tested their inhibition of type I simple Pharmacological activity of herpes virus HSV-1, in order to obtain new drugs or lead compounds that inhibit HSV-1 virus independent intellectual property rights

Method used

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  • Application of lignin flavanonol in preparation of antiviral drugs
  • Application of lignin flavanonol in preparation of antiviral drugs

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Example 1 : the preparation of intermediate epoxy chalcone (4)

[0021] 1.12, The preparation of 4,6-trimethoxymethoxyacetophenone (1):

[0022] 2.6 grams of sodium hydride in 40 milliliters of DMF was cooled in an ice-water bath, and a mixed solution of 5.6 grams of 2,4,6-trihydroxyacetophenone in 60 milliliters of benzene and 7.0 milliliters of DMF was added dropwise under nitrogen protection, and cooled in an ice bath 9.0 ml of chloromethyl ether solution was added dropwise, and stirred at room temperature for 24 hours. Pour into 100 ml of 10% sodium hydroxide aqueous solution, extract with ether 3 times, 50 ml each time, wash with saturated sodium bicarbonate, dry over anhydrous sodium sulfate, filter, concentrate, 40 g of 200-300 mesh silica gel column chromatography, petroleum Ether / ethyl acetate 4:1 was eluted to obtain 7.0 g of compound (1). Yellow oil; R f (Petroleum ether / ethyl acetate=3:1): 0.30; H NMR spectrum (400MHz, deuterated chloroform): δ2.52 (sing...

Embodiment 2

[0029] Example 2 : Preparation of (±)-2-(2,3-dihydroxyphenyl)2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one (5)

[0030] 1.0 grams of intermediate epoxy chalcone (4) was dissolved in 15 milliliters of methanol, and added under stirring to 10 milliliters of methanol solution in which 1.5 milliliters of concentrated hydrochloric acid was dissolved, and the temperature was raised to 60° C. for half an hour, then the heating was removed, and after cooling, the The solvent was removed by pressure evaporation, 50 ml of water was added to the residue, extracted with ethyl acetate (3 times, 20 ml each), the combined organic layers were washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, and evaporated under reduced pressure. After removing the solvent, the residue was subjected to 20 g of 200-300 mesh silica gel column chromatography, eluting with petroleum ether / ethyl acetate 3:1 to obtain 97 mg of (±)-2-(2,3-dihydroxyphenyl) 2 , 3-Dihydro-3,5,7-tr...

Embodiment 3

[0031] Example 3 : (±)-2-[2,3-dihydro-2-(4-hydroxyphenyl)-3-hydroxymethyl-1,4-benzodioxane-5]-2,3-dihydro - Preparation of 3,5,7-trihydroxy-4H-1-benzopyran-4-one

[0032] Put 0.22 grams of silver carbonate into the dry reaction bottle, add 20 milliliters of anhydrous benzene and 5 milliliters of anhydrous acetone, add dropwise 90 milligrams of (±)-2-(2,3-dihydroxyphenyl) 2,3 -dihydro-3,5,7-trihydroxy-4H-1-chromen-4-one (5) in dry benzene in 5 ml and 76 mg of p-hydroxycinnamyl alcohol in dry acetone in 3 ml, The reaction was incubated at 55°C for 20 hours. After cooling to room temperature, let it stand, filter off the insoluble matter, and concentrate the mother liquor under reduced pressure to obtain a yellow oil, which was subjected to 20 g of 200-300 mesh silica gel column chromatography and eluted with chloroform / methanol 10:1 to obtain 18 mg of the target compound.

[0033] (±) 2-[2,3-dihydro 2-(4-hydroxyphenyl)-3-hydroxymethyl-1,4 benzodioxane-5]-2,3-dihydro-3, 5,7-...

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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 virus infection caused by herpes simplex virus HSV-1 and / or drugs for curing oral ulcer. The chemical compound is prepared by chemical synthesis, pharmacological experiments shows that, the chemical compound has powerful inhibitory action to the herpes simplex virus HSV-1, and the half inhibitory concentration value IC[50] is 39.41 mg / mL.

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 (±)-2-[2,3-dihydro-2-(4-hydroxyphenyl)-3 -Hydroxymethyl-1,4-benzodioxane-5]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one or its druggable Use of salt for preparing medicine for inhibiting virus infection caused by herpes simplex virus HSV-1 and / or treating oral ulcer. Background technique [0002] Herpes simplex virus can be divided into two types: type I and type II. Type I herpes virus (HSV-1) mainly infects the skin, mucous membranes and organs above the waist. HSV-1 is mainly transmitted through close contact with the respiratory tract, skin and mucous membranes. 99% Inflammation and herpes of the oral mucosa, nasal vestibule, conjunctiva, throat, and herpes around the mouth are all caused by type I herpes virus infection. Herpes simplex virus is widely prevalent in the wo...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P31/22A61P1/04
Inventor 李校堃龚景旭黄可新李海波任琦巫秀美白骅赵昱瞿佳
Owner WENZHOU MEDICAL UNIV
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