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Silybin flavonolignan and their production method and use

A technology of lipids and medicinal salts, applied in the field of organic chemistry and medicinal chemistry, can solve problems such as insufficient water solubility and bioavailability, and limited drug market

Inactive Publication Date: 2009-08-19
ZHEJIANG HISUN PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Silybin compounds have definite curative effect, but the market of this drug is limited due to some shortcomings in water solubility and bioavailability

Method used

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  • Silybin flavonolignan and their production method and use
  • Silybin flavonolignan and their production method and use
  • Silybin flavonolignan and their production method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Compound 1-3-1 (1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-methoxyphenyl ) propenone) preparation:

[0040]

[0041] 3 grams of 3-methoxy-4,5-dimethoxymethoxybenzaldehyde and 3.5 grams of 2,4,6-trimethoxymethoxyacetophenone were dissolved in 40mL of ethanol, and 10g of potassium hydroxide was added 20 mL of aqueous solution 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 4.4 g of compound 1-3-1 yellow oil by column chromatography. Yield 70%.

[0042] R f (PET / EtOAc=2:1)0.36; UV(MeOH)λ max =208,321nm; 1 H NMR (400MHz, deuterated chloroform) δ: 3.34(s, 6H, OCH 3 ), 3.43 (s, 3H, OCH 3 ), 3.46(s, 3H, OCH 3 ), ...

Embodiment 2

[0044] Example 2: Compound 1-3-2 (1-(2,4,6-trimethoxymethoxyphenyl)-3-(3,4-dimethoxymethoxy-5-ethoxyphenyl ) propenone) preparation:

[0045]

[0046] R f (PET / EtOAc=2:1)0.40; UV(MeOH)λ max =210,325nm; 1 H NMR (400MHz, deuterated chloroform) δ: 1.39(t, J=7.2Hz, 3H, CH 3 ), 3.34(s, 6H, OCH 3 ), 3.43 (s, 3H, OCH 3 ), 3.46(s, 3H, OCH 3 ), 3.56(s, 3H, OCH 3 ), 4.02 (q, J=7.2Hz, 2H, CH 2 ), 5.06(s, 4H, OCH 2 O), 5.11(s, 4H, OCH 2 O), 5.14(s, 2H, OCH 2 O), 6.51(s, 2H, H-3', 5'), 6.74(d, J=1.6Hz, 1H, H-2), 6.80(d, J=16.0Hz, 1H, H-α), 6.91(d, J=1.6Hz, 1H, H-6), 7.17(d, J=16.0Hz, 1H, H-β); ESI-MS: 553(M+1) + .

Embodiment 3

[0047] Example 3: Compound 1-4-1 (1-(2,4,6-trimethoxymethoxyphenyl)-3-(3-methoxy-4,5-dimethoxymethoxyphenyl ) the preparation of propylene oxide):

[0048]

[0049] Dissolve 3 g of compound 1-3-1 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, acetic acid Ethyl ether extraction (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 yellow oil with a yield of 85%, which could be directly used in the next reaction.

[0050] R f (PET / EtOAc=2:1)0.37; UV(MeOH)λ max =205,278nm; 1 H NMR (400MHz, deuterated chloroform) δ: 3.34(s, 6H, OCH 3 ), 3.43 (s, 3H, OCH 3 ), 3.46(s, 3H, OCH 3 ), 3.56(s, 3H, OCH 3 ), 3.87 (s, 3H, OCH 3 ), 3.89(d, J=1.6Hz, 1H, H-β), 3.93(d, J=1.6Hz, 1H, H-α), 5.06(s, 4H, OCH 2 O), ...

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Abstract

The invention relates to a silibinin flavonoid lignan compound with anti-free radical oxidation, liver protection, prevention and treatment of senile dementia and anti-aging activities and a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to the preparation method of the compound of formula (1) including its important intermediates and its pharmaceutical composition and medical application. The compound of the present invention has anti-oxidative damage protective effect on the primary cells of SD neonatal rats, and can be expected to be used as a medicine for preventing liver damage; Radicals, the activity of inhibiting the generation of lipid peroxides induced by free radicals, and the strong anti-free radical-induced damage to PC12 cells, so it can be expected to be a drug for treating various diseases caused by free radicals.

Description

field of invention [0001] The invention belongs to the field of organic chemistry and medicinal chemistry. Specifically, the invention relates to a preparation method and application of a novel silybin flavonoid lignan, which are obtained through a total synthesis method. The compounds of the present invention and their intermediates have protective effects against oxidative damage to primary liver cells of SD neonatal rats, and at the same concentration, their ability to resist oxidative damage to cells is much higher than that of the positive control quercetin, which can It is expected to be used as a drug for preventing liver damage; the present invention has tested the anti-oxidant free radical activity of this type of compound, and found that it has the functions of scavenging superoxide anion free radicals in vitro, scavenging diphenylpicrylphenylhydrazine free radicals, inhibiting free radicals Induced lipid peroxide generation activity, the above activity shows that th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/02A61K31/357A61P1/16A61P25/28A61P29/00A61P35/00A61P37/02A61P37/08A61P39/06A61P9/10
Inventor 赵昱陶巧凤汪峰龚景旭冯玉冰白骅刘伟周长新巫秀美曾苏
Owner ZHEJIANG HISUN PHARMA CO LTD
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