Novel application of sulfonic benzo-gamma-pyrone compound

A compound and pyrone technology, applied in the field of sulfobenzo-γ-pyrone compounds, can solve the research on the anti-HIV activity of sulfobenzo-γ-pyrone compounds that have not been seen reports and other issues

Inactive Publication Date: 2010-02-24
李泽琳 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The use of sulfonic acid benzo-γ-pyrone compounds disclosed in the prior art is mainly used for anti-hepatitis B virus [8] ,anti-oxidation [9，10，14] , treatment of cardiovascular and cerebrovascular diseases [11] and anti-tumor [12，13] , there is no report on the anti-HIV activity of sulfobenzo-γ-pyrone compounds

Method used

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  • Novel application of sulfonic benzo-gamma-pyrone compound
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  • Novel application of sulfonic benzo-gamma-pyrone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Sodium 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-benzo-γ-pyrone-8-sulfonate (also known as: sodium quercetin-8-sulfonate) preparation of

[0079] methods according to the prior art [5，6], add 1.0g of quercetin powder to 4mL of concentrated sulfuric acid under rapid stirring, react at 0-50°C for 2-6h, add 50mL of saturated sodium chloride solution, let stand, filter under reduced pressure, filter cake with saturated chloride Wash with sodium solution (5mL×3), and filter to dryness with suction to obtain an orange-yellow product. The product was recrystallized three times with distilled water, recrystallized once with absolute ethanol, freeze-crystallized, filtered under reduced pressure, and dried to obtain 1.15 g of amorphous crystals, namely 2-(3,4-dihydroxyphenyl)-3,5,7 -Sodium trihydroxy-benzo-γ-pyrone-8-sulfonate (compound 1), yield 86%.

[0080] 1 H NMR (DMSO-d 6 )δ6.15 (1H, s, H-6), 8.00 (1H, d, J=2.0Hz, H-2'), 6.87 (1H, d, J=8.4Hz, H-5'), 7.89 ( 1H, dd, J=2....

Embodiment 2

[0082] Preparation of 3-(3-sodium sulfonate-4-hydroxyphenyl)-7-hydroxy-benzo-γ-pyrone (also known as: daidzein-3′-sodium sulfonate) [9]

[0083] Add 0.762g of daidzein powder to 4mL of concentrated sulfuric acid under rapid stirring, react at 0-50°C for 2-6h, add 50mL of saturated sodium chloride solution, let stand, filter under reduced pressure, filter cake with saturated sodium chloride The solution (5mL×3) was washed and suction filtered to dryness to obtain a light yellow powder. The resulting product was recrystallized three times by distilled water, once by absolute ethanol, freeze-crystallized, suction-filtered under reduced pressure, and dried to obtain 0.96 g of amorphous crystals, namely 3-(3-sodium sulfonate-4-hydroxyphenyl)-7 -Hydroxy-benzo-γ-pyrone (compound 2), yield 90%.

[0084] 1 H NMR (DMSO-d 6 )δ8.34 (1H, s, H-2), 7.76 (1H, d, J=8.4Hz, H-5), 6.66 (1H, d, J=8.4Hz, H-6), 6.45 (1H, s, H-8), 7.66 (1H, d, J=2.0Hz, H-2′), 6.80 (1H, d, J=8.4Hz, H-5′), 7.37 (1...

Embodiment 3

[0086] Preparation of 3-(3-sodium sulfonate-4,5-dihydroxyphenyl)-7-hydroxy-benzo-γ-pyrone (also known as: genistein-3′-sodium sulfonate) [9，11]

[0087] Add 0.81g of genistein powder to 4mL of concentrated sulfuric acid under rapid stirring, react at 0-50°C for 2-6h, add 50mL of saturated sodium chloride solution, let it stand, filter under reduced pressure, filter cake with saturated sodium chloride The solution (5mL×3) was washed and suction filtered to dryness to obtain a light yellow powder. The resulting product was recrystallized three times with distilled water, once with absolute ethanol, freeze-crystallized, filtered under reduced pressure, and dried to obtain 0.90 g of amorphous crystals, namely 3-(3-sodium sulfonate-4,5-dihydroxyphenyl )-7-hydroxy-benzo-γ-pyrone (compound 3), yield 81%.

[0088] 1 H NMR (DMSO-d 6 )δ8.49 (1H, s, H-2), 6.26 (1H, d, J=2.0Hz, H-6), 6.43 (1H, d, J=2.0Hz, H-8), 7.71 (1H, d, J=2.0Hz, H-2'), 6.86 (1H, d, J=8.4Hz, H-5'), 7.39 (1H, dd, J...

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Abstract

The invention relates to novel application of a sulfonic benzo-gamma-pyrone compound, in particular to the application of the sulfonic benzo-gamma-pyrone compound represented by a general formula (I) to HIV virus inhibition, wherein the substituents R1, R2, R3, R4, R5 and R6 of the general formula(I) are defined in the description.

Description

technical field [0001] The present invention relates to a new application of sulfobenzo-γ-pyrone compound, especially the application of inhibiting HIV virus. Background technique [0002] AIDS is the abbreviation of "Acquired Immune Deficiency Syndrome" (Acquired Immune Deficiency Syndrome--AIDS), which is an infectious disease caused by human immunodeficiency virus (HIV, also known as AIDS virus). AIDS is a serious infectious disease in which the immune system of the human body is destroyed by the AIDS virus, making the human body lose its resistance to various life-threatening pathogens, resulting in various infections or tumors, and finally leading to death. Over the years, the international community has made active efforts to prevent and control AIDS, and the prevention and control work has made some progress, but the spread of AIDS around the world has not yet been effectively controlled. With the rapid spread of AIDS, AIDS prevention has become an important public h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/352A61P31/18
Inventor 李泽琳赵伟杰杨怡姝李悦青曾毅王世盛岑山马洪涛王小利刘伟
Owner 李泽琳
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