Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

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: 2007-07-04
ZHEJIANG HISUN PHARMA CO LTD
View PDF0 Cites 19 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • 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 ) Preparation of propylene ketone):

[0040]

[0041] 3 grams of 3-methoxy-4,5-dimethoxymethoxybenzaldehyde and 3.5 grams of 2,4,6-trimethoxymethoxyacetophenone are dissolved in 40mL ethanol, and 10g potassium hydroxide is added. 20mL aqueous solution, stirred at room temperature for 15 hours. Ethanol was evaporated under reduced pressure, 30 mL of water was added, and extraction with ethyl acetate (3×20 mL). After the organic phases were combined, they were washed with saturated sodium bisulfite (40 mL) and saturated brine (40 mL) successively, dried over anhydrous sodium sulfate, filtered and concentrated, and 4.4 g of compound 1-3-1 as a yellow oil was obtained by column chromatography. The yield was 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) ) Preparation of propylene ketone):

[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 = 1.6 Hz, 1H, H-2), 6.80 (d, J = 16.0 Hz, 1H, H-α), 6.91 (d, J = 1.6 Hz, 1H, H-6), 7.17 (d, J = 16.0 Hz, 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 ) Preparation of epoxy acetone):

[0048]

[0049] 3 g of compound 1-3-1 was dissolved in 50 ml of methanol, and while stirring, 4 mL of 2N sodium hydroxide and 4 mL of 30% hydrogen peroxide were added, and stirred at room temperature for 10 hours. The solvent was evaporated under reduced pressure, and 50 mL of water and acetic acid were added. Ethyl extraction (3×30 mL). The organic phases were combined, washed with saturated brine (40 mL), and dried over anhydrous sodium sulfate. It was filtered and concentrated to obtain 2.6 g of yellow oil with a yield of 85%, which can 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), ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to a silibinin flavonolignan and its medicine salt or solvates. The invention also relates to the method preparing its important mediate and its drug combination and medical application. The compound can protect primary hepatocyte from oxidative damage for SD newly born rat hepatitis virus, so it is expected to be used as drug preventing liver damage. The compound can remove superoxide anion free radical and diphenyl picryl phenylhydrazine free radical, inhibit free radical from inducing generation of fat oxidatant, protect PC 12 cell from being damaged by free radical, so it is expected to be used as drug treating diseases caused by free radical.

Description

Invention field [0001] The present invention belongs to the field of organic chemistry and medicinal chemistry. Specifically, the present invention relates to a preparation method and application of a new type of silibinin-like flavonoid lignans, which are obtained by a total synthesis method. The compound of the present invention and its intermediates have an anti-oxidative damage protection effect on primary liver cells of SD neonatal rats, and at the same concentration, their anti-oxidative damage ability to cells is much higher than that of the positive control quercetin. It is expected to be used as a drug to prevent liver damage; the present invention also tested the anti-oxygen free radical activity of this type of compound, and found that it has the ability to scavenge superoxide anion free radicals, scavenge diphenylpicryl phenylhydrazine free radicals and inhibit free radicals The activity of induced lipid peroxide production. The above activities indicate that this type...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com