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E-ring substituted silybin derivative and preparation method and medical application thereof

A technology of silibinin and derivatives, which is applied in the field of preparation of silybin derivatives, and achieves the effects of simple preparation method, protection of brain nerve cells, and less pollution

Inactive Publication Date: 2010-07-21
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the continuing investigation, we found that there are very few reports on the modification of the silybin E ring

Method used

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  • E-ring substituted silybin derivative and preparation method and medical application thereof
  • E-ring substituted silybin derivative and preparation method and medical application thereof
  • E-ring substituted silybin derivative and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1: the preparation of compound I-b-1 (3-allyl-4-hydroxycinnamic acid ethyl ester)

[0035]

[0036] 0.30 g of 3-allyl-4-hydroxybenzaldehyde (2 mmol), 0.70 g of phosphorus ylide (2 mmol) were dissolved in 10 ml of chloroform, heated to reflux for 5 hours, and the solvent was removed by distillation under reduced pressure, and the residue was passed through the column Chromatography gave 0.30 g of a white solid, with a yield of 65%. R f (petroleum ether: ethyl acetate=3:1)=0.29, H NMR spectrum 1 H NMR (400MHz, deuterated chloroform) δ: 1.33(t, J=7.2Hz, 3H, CH 3 ), 3.42 (d, J=6.4Hz, 2H, OCH 2 CH=), 4.25(q, J=7.2Hz, 2H, OCH 2 ), 5.16 (d, J=7.2Hz,=CH 2 a), 5.20(s, 1H, =CH 2 b), 6.00(m, 1H, CH=CH 2 ), 6.29 (d, J=16.0Hz, 1H, H-8), 6.81 (d, J=8.0Hz, 1H, H-6), 7.31 (d, J=8.0Hz, 1H, H-5), 7.31(s, 1H, H-2), 7.61(d, J=16.0Hz, 1H, H-7), electrospray mass spectrometry ESI-MS: 233[M+H] + .

Embodiment 2

[0038] Embodiment 2: the preparation of I-b-2 (3-methoxy-4-hydroxyl-5-allyl cinnamic acid ethyl ester)

[0039]

[0040] Yellow oil; Yield: 74%; R f (petroleum ether: ethyl acetate=3:1)=0.25, H NMR spectrum 1 H NMR (400MHz, deuterated chloroform) δ: 1.33(t, J=7.2Hz, 3H, CH 3 ), 3.40 (d, J=6.8Hz, 2H, OCH 2 CH=), 3.91(s, 3H, OCH 3 ), 4.25 (q, 2H, CH 2 ), 5.09 (m, 2H, CH 2 =), 6.00 (m, 1H, CH 2 =CH), 6.28(d, J=16.0Hz, 1H, H-8), 6.92(d, J=2.0Hz, 1H, H-6), 6.96(d, J=2.0Hz, 1H, H-2 ), 7.59 (d, J=16.0 Hz, 1H, H-7). Embodiment 3: Preparation of I-b-5 (3-chloro-4-hydroxyl-5-methoxycinnamic acid ethyl ester)

Embodiment 3

[0040] Yellow oil; Yield: 74%; R f (petroleum ether: ethyl acetate=3:1)=0.25, H NMR spectrum 1 H NMR (400MHz, deuterated chloroform) δ: 1.33(t, J=7.2Hz, 3H, CH 3 ), 3.40 (d, J=6.8Hz, 2H, OCH 2 CH=), 3.91(s, 3H, OCH 3 ), 4.25 (q, 2H, CH 2 ), 5.09 (m, 2H, CH 2 =), 6.00 (m, 1H, CH 2 =CH), 6.28(d, J=16.0Hz, 1H, H-8), 6.92(d, J=2.0Hz, 1H, H-6), 6.96(d, J=2.0Hz, 1H, H-2 ), 7.59 (d, J=16.0 Hz, 1H, H-7). Embodiment 3: Preparation of I-b-5 (3-chloro-4-hydroxyl-5-methoxycinnamic acid ethyl ester)

[0041]

[0042] Pale yellow solid; Yield: 63%; R f (petroleum ether: ethyl acetate=3:1)=0.40, H NMR spectrum 1 H NMR (400MHz, deuterated chloroform) δ: 1.34(t, J=7.2Hz, 3H, CH 3 ), 3.86(s, 3H, OCH 3 ), 4.27 (q, J=7.2Hz, 2H, CH 2 ), 6.38(d, J=16.0Hz, 1H, H-8), 6.98(d, J=2.0Hz, 1H, H-6), 7.20(d, J=2.0Hz, 1H, H-2), 7.56 (d, J=16.0 Hz, 1H, H-7).

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Abstract

The invention relates to an E-ring substituted silybin derivative and a preparation method and medical application thereof, in particular to synthesis of the E-ring substituted silybin derivative and medical application of the compound or the pharmaceutically acceptable salts of the compound in preparing the medicines for preventing physiological disorders or diseases caused by oxidative stress. The compound has the activity of protecting the hydrogen peroxide induced rat adrenal pheochromocytoma (PC12) cell from injury, namely having the anti-oxidative injury protection effect on the PC12 cell simulating the brain nerve cell, and also has the activity of suppressing xanthine oxidase, thus the compound can be expectedly developed to have the medical applications in preparing the medicines for preventing the neurodegenerative diseases such as oxidation of the brain nerve cell, senile dementia and the like, and the medicines for preventing the diseases caused by xanthine oxidase, such as gout.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry and medicine, in particular, the invention relates to a preparation method and application of a class of E-ring substituted silybin derivatives. This type of compound is obtained through a synthetic method, and the pharmacological tests on this type of compound show that: this type of compound exhibits a strong anti-hydrogen peroxide-induced damage to rat adrenal pheochromoma cells (PC12 cells), that is, to simulated brain nerve cells. The PC12 cells have the protective effect against oxidative damage, indicating that it has a positive effect on protecting brain cell tissue against oxidation and cranial nerves, preventing and treating senile dementia, and can be expected to be used in the preparation of drugs for preventing and treating such neurodegenerative diseases. Furthermore, the compound also shows a certain inhibitory effect on xanthine oxidase, and can be expected to be used for p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/04A61K31/357A61P25/00A61P25/28A61P25/16A61P25/14A61P19/06A61P1/16A61P39/06
Inventor 赵昱龚景旭刘光明杨雷香巫秀美汪峰彭芳谭仁祥曾苏
Owner DALI UNIV
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