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Flavanonol compounds and their production method and use

A technology of dihydroflavonol and trimethoxydihydroflavonoids, which is used in medical preparations containing active ingredients, drug combinations, organic chemistry and other directions

Inactive Publication Date: 2007-07-04
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

And 5,6,7- trioxide substituted dihydroflavonols have not been reported

Method used

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  • Flavanonol compounds and their production method and use
  • Flavanonol compounds and their production method and use
  • Flavanonol compounds and their production method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1: Preparation of compound I-2-1 (6-methoxymethoxy-2,3,4-trimethoxyacetophenone)

[0051]

[0052] 1.5 grams of 6-hydroxyl-2,3,4-trimethoxyacetophenone was dissolved in 20 milliliters of dichloromethane, and then 1.5 grams of sodium hydroxide was dissolved to obtain 20 milliliters of water and 0.4 gram of tetrabutylammonium bromide, Stir and cool down to 0°C, slowly add 1.5 ml of distilled chloromethyl ether, stir at room temperature for 12 hours, let stand, separate the organic layer, extract the aqueous layer with 10 ml of dichloromethane three times, combine them, and wash with saturated saline After washing, drying over sodium sulfate, filtering, and concentration, the residue was subjected to column chromatography to obtain 1.4 g of light yellow oil, with a yield of 80%. Rf (petroleum ether / ethyl acetate=3:1): 0.21, 1 H NMR (400MHz, deuterated chloroform) δ: 2.56(s, 3H, CH 3 ), 3.78(s, 3H, OCH 3 ), 3.85(s, 3H, OCH 3 ), 3.90 (s, 3H, OCH 3 ), 5.15(...

Embodiment 2

[0053] Embodiment 2: Preparation of compound I-2-2 (2,4-dimethoxy-3,6-dimethoxymethoxyacetophenone):

[0054]

[0055] 1.76 grams of 3,6-dihydroxy-2,4-dimethoxyacetophenone was dissolved in 20 milliliters of dichloromethane, and then 1.5 grams of sodium hydroxide was added to obtain 20 milliliters of water and 0.4 grams of tetrabutyl bromide ammonium, stirred and cooled to 0°C, slowly added 1.5 ml of distilled chloromethyl ether, stirred at room temperature for 12 hours, stood still, separated the organic layer, extracted three times with 10 ml of dichloromethane and combined the aqueous layer with saturated Washed with brine, dried over sodium sulfate, filtered, concentrated, and the residue was subjected to column chromatography to obtain 1.63 g of light yellow oil with a yield of 82%. Rf (petroleum ether / ethyl acetate=3:1): 0.30, 1 H NMR (400MHz, deuterated chloroform) δ: 2.48(s, 3H, CH 3 ), 3.60 (s, 3H, OCH 3 ), 3.85(s, 3H, OCH 3 ), 3.86(s, 3H, OCH 3 ), 5.05(s, 2H,...

Embodiment 3

[0059] Embodiment 3: Preparation of compound I-4-1 (6,4'-dimethoxymethoxy-2,3,4-trimethoxychalcone)

[0060]

[0061] 1.6 grams of I-2-1 were dissolved in 60 milliliters of methanol with 0.5 grams of potassium hydroxide, then 1.5 grams of p-methoxybenzaldehyde was added, and after stirring at room temperature for 8 hours, the solvent was evaporated under reduced pressure, and the residue was Add 30 milliliters of water, extract three times with 20 milliliters of ethyl acetate, combine the organic phases and wash with saturated brine, dry over sodium sulfate, filter, and concentrate the filtrate, and the residue is subjected to injection chromatography to obtain 2.1 grams of light yellow oil, with a yield of 84 %.

[0062] Rf (petroleum ether / ethyl acetate=3: 1)=0.13; 1 H NMR (400MHz, deuterated chloroform) δ: 3.41(s, 3H, OCH 3 ), 3.47 (s, 3H, OCH 3 ), 3.84(s, 3H, OCH 3 ), 3.85(s, 3H, OCH 3 ), 3.90 (s, 3H, OCH 3 ), 5.10 (s, 2H, OCH 2 O), 5.20(s, 2H, OCH 2 O), 6.57(s,...

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PUM

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Abstract

The invention relates to a novel 5, 6, 7- tri-oxygen Dihydroflavonol, shown in formula (1), the preparation method and its application. The compound can be used to prepare drug combination that can prevent hepatitis b, protect liver, treat fungal infection, prevent diseases that generates free radical during disease change including inflammation, autoimmune diseases, radiotherapy sequela, tumor, myocardial ischemia, cardiac hypertrophy, aging, allergic reaction and atherosclerosis. There are various preparations for said drug combination.

Description

technical field [0001] The invention belongs to the field of organic chemistry and medicinal chemistry, specifically, the invention relates to a class of novel 5,6,7- Trioxygen-substituted dihydroflavonol compound and its preparation method and use. Background technique [0002] Dihydroflavonols are widely found in natural products, and research on their activity has gradually become more active this year. Recent studies have shown that dihydroflavonols have antioxidant, antifungal and antitumor activities (Yeom, Seung-Hwan, etc., Saengyak Hakhoechi (2003), 34 (4), 344-351; Piccinelli, AL, etc., Journal of Agricultural and Food Chemistry (2004), 52(19), 5863-5868). Recent studies on its antioxidant activity have shown that it can increase the activity of red blood cells, liver and myocardial SOD (superoxide dismutase) in mice, reduce the level of LPO (lipid peroxygen compounds) in plasma, liver and heart, and reduce brain edema The LPO content in animal blood and brain ti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/32C07D303/32C07C49/255A61K31/352A61P31/12A61P1/16A61P31/10A61P39/06A61K9/00
Inventor 赵昱汪峰刘伟白骅
Owner ZHEJIANG HISUN PHARMA CO LTD
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