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Pharmacy use of ethyoxyl substituted silybin for inhibiting herpes simplex virus

An ethoxy and purpose technology, which is applied in the field of pharmaceutical use of ethoxy to replace silibinin to inhibit herpes simplex virus, can solve problems such as not being effectively developed, and achieves simple synthesis route, high yield, and is beneficial to industrial production. Effect

Inactive Publication Date: 2011-05-04
WENZHOU MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The silybin compounds have the exact multiple curative effects described above, but their new uses in antiviral aspects, especially the inhibition of herpes simplex virus, have not been effectively developed. Therefore, we have prepared water with different substitutions for the B ring and the E ring. Silybin derivatives, and tested their pharmacological activity of inhibiting herpes simplex virus type I HSV-1, in order to obtain new drugs for inhibiting HSV-1 virus with independent intellectual property rights

Method used

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  • Pharmacy use of ethyoxyl substituted silybin for inhibiting herpes simplex virus
  • Pharmacy use of ethyoxyl substituted silybin for inhibiting herpes simplex virus
  • Pharmacy use of ethyoxyl substituted silybin for inhibiting herpes simplex virus

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1 : the preparation of compound 3 [1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl) propenone]

[0019]

[0020] 3 grams of 3-ethoxy-4,5-dimethoxymethoxybenzaldehyde and 3.5 grams of 2,4,6-trimethoxymethoxyacetophenone were dissolved in 40 milliliters of ethanol, and dissolved with 10 grams of hydrogen A 20 ml aqueous solution of potassium oxide was stirred at room temperature for 15 hours. Ethanol was distilled off under reduced pressure, 30 ml of water was added, and extracted with ethyl acetate (3×20 ml). After combining the organic phases, they were washed successively with saturated sodium bisulfite (40 ml) and saturated brine (40 ml), dried over anhydrous sodium sulfate, concentrated by filtration, and obtained compound 3[1-(2,4, 4.4 g of 6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl)propenone] yellow oil, yield 70%. R f (petroleum ether / ethyl acetate=2 / 1): 0.40; UV (methanol) λ max =210,325nm; H NMR spe...

Embodiment 2

[0021] Example 2 : Compound 4 [1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl) oxide acetone]

[0022]

[0023] Get the compound 1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl) propenone obtained in Example 1 Dissolve 3 g in 50 ml of methanol, add 4 ml of 2N sodium hydroxide and 4 ml of 30% hydrogen peroxide under stirring, stir at room temperature for 10 hours, evaporate the solvent under reduced pressure, add 50 ml of water, and extract with ethyl acetate (3 x 30 ml). The organic phases were combined, washed with saturated brine (40 mL), and dried over anhydrous sodium sulfate. Filtration and concentration gave 2.6 g of a yellow oily substance, with a yield of 85%.

[0024] 1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl)epoxyacetone: R f (petroleum ether / ethyl acetate=2 / 1): 0.40; UV (methanol) λ max =206,281nm; H NMR spectrum 1 H NMR (400MHz, deuterated chloroform) δ: 1.39 (triplet, J=7.2...

Embodiment 3

[0025] Example 3 : Preparation of compound 5 [(±) 5'-ethoxyl-3,5,7,3',4'-pentahydroxydihydroflavone]:

[0026]

[0027] 2.8 g of compound 4 [1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl) glycidone] dissolved In 35 milliliters of methanol and 15 milliliters of tetrahydrofuran, add 5 milliliters of concentrated hydrochloric acid dropwise, stir at 50-55 ° C for 30 minutes, evaporate the solvent under reduced pressure, extract with ethyl acetate (3 × 30 milliliters), combine the organic phases and use Wash with saturated brine (40 ml), and dry over anhydrous sodium sulfate. After filtration, concentration, and column chromatography, 0.75 g of yellow powder was obtained, with a yield of 45%.

[0028] R f (chloroform / methanol=10 / 1): 0.15; H NMR spectrum 1 H NMR (400MHz, deuterated acetone) δ: 1.33 (triplet, J=7.2Hz, 3H, CH 3 ), 4.08 (quartet, J=7.2Hz, 2H, CH 2 ), 4.62 (double doublet, J=12.0, 4.0Hz, 1H, H-3), 4.68 (doublet, J=4.0Hz, 1H, 3-OH), 4...

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Abstract

The invention relates to a pharmaceutical use of ethoxy-substituted silibinin for inhibiting herpes simplex virus. More particularly, the invention relates to an ethoxy-substituted silibinin derivative on a ring B, namely, the use of compound (cis-trans)2-(2, 3-dihydro-3-(4-hydroxyl-3-methoxyphenyl)-2-hydroxymethyl-8-ethoxy-1, 4-benzo dioxane-6-)-2, 3-dihydro-3, 5, 7-trihydroxy-4H-1-chromene-4-ketone) or pharmaceutically acceptable salts thereof in the preparation of medicines for the treatment of virus infection and / or canker sore caused by the herpes simplex virus HSV-1. The compound is acquired by synthesis according to chemical methods, and pharmacological experiments show that the compound has strong inhibition effect on the herpes simplex virus HSV-1 with the IC50 value thereof being 41.07 microgram / milliliter.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a silibinin derivative substituted with ethoxy group on the B ring, namely the compound (±)2-[2,3-dihydro-3-(4-hydroxyl- 3-methoxyphenyl)-2-hydroxymethyl-8-ethoxy-1,4-benzodioxane-6-]-2,3-dihydro-3,5,7-tri Hydroxy-4H-1-benzopyran-4-one] or a pharmaceutically acceptable salt thereof is used in the preparation of medicines for treating viral infections and / or oral ulcers caused by herpes simplex virus HSV-1. Background technique [0002] Herpes simplex virus (HSV) is widely prevalent in the world, and its infection rate in developed countries such as the United States: 20-40% (childhood), 50-70% (adulthood). Humans are the only host of herpes simplex virus. The diameter of the virus is about 120-150 microns. The nucleus containing DNA is located in the middle, and outwards are composed of three concentric structures: envelope, body coat, and...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/357A61P31/22A61P1/04
Inventor 黄可新苏杭龚景旭王彦广潘映秋谢金菡钟韵伟赵昱瞿佳李校堃
Owner WENZHOU MEDICAL UNIV
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