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Preparation method of abrusamide

A technology of grass A and feather chicken, which is applied in the preparation of organic compounds, carboxylate salts, carboxylic acid amides, etc., can solve the problem that the separation and purification of chicken bone grass cannot meet the needs of the market, so as to reduce the temperature, The effect of abundant raw material source and high yield

Inactive Publication Date: 2019-06-04
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no report on the chemical synthesis of Abrusamide chrysanthemum. With the continuous deepening of the research and development of chrysanthemum, a large amount of Abrusamide is needed for clinical application. The separation and purification from chrysanthemum meets Can't meet market demand

Method used

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  • Preparation method of abrusamide
  • Preparation method of abrusamide
  • Preparation method of abrusamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Preparation of 4,4'-dihydroxy-α-hiseric acid

[0023] Taking p-hydroxycinnamic acid and diisopropylethylamine as reactants, adding it to the solvent acetonitrile, the ratio of p-hydroxycinnamic acid, diisopropylethylamine and solvent by weight is 1:2:10, and then Add 1% photocatalyst [Ru(bpy) of p-hydroxycinnamic acid weight 3 ]Cl 2 Stir evenly, then irradiate with visible light for 5 hours to obtain the crude product, and then recrystallize to obtain the product 4,4'-dihydroxy-α-hiseric acid.

[0024] White crystal, Mp>300℃.Anal.Calcd for C 18 h 16 o 6 :C,65.85%;H,4.91%.Found:C,65.76%;H,4.93%.Positive FAB-MS

[0025] m / z:329[M+H] + . 1 H-NMR (DMSO-d6)d: 3.65 (2H, m), 4.14 (2H, m), 6.70 (4H, d, J = 8.8Hz), 7.12 (4H, d, J = 8.8Hz).

[0026] (2) Preparation of Abrusamide

[0027] 4,4'-dihydroxy-α-hiseric acid and tyrosine obtained in step (1), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, three Ethylamine, 4-dimethylaminopyridine and dichlorome...

Embodiment 2

[0030] (1) Preparation of 4,4'-dihydroxy-α-hiseric acid 2

[0031] Taking p-hydroxycinnamic acid and diisopropylethylamine as reactants, adding the solvent to acetonitrile, the ratio of p-hydroxycinnamic acid, diisopropylethylamine and solvent in parts by weight is: 1:2.5:13, and then 3% photocatalyst [Ru(bpy) 3 ]Cl 2 Stir evenly, then irradiate with visible light for 8 hours to obtain the crude product, and then recrystallize to obtain the product 4,4'-dihydroxy-α-hiseric acid.

[0032] White crystal, Mp>300℃.Anal.Calcd for C 18 h 16 o 6 :C,65.85%;H,4.91%.Found:C,65.76%;H,4.93%.Positive FAB-MS

[0033] m / z:329[M+H] + . 1 H-NMR (DMSO-d6)d: 3.65 (2H, m), 4.14 (2H, m), 6.70 (4H, d, J = 8.8Hz), 7.12 (4H, d, J = 8.8Hz).

[0034] (2) Preparation of Abrusamide

[0035] 4,4'-dihydroxy-α-hiseric acid and tyrosine obtained in step (1), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, three Ethylamine, 4-dimethylaminopyridine and dichloromethane are mixed according ...

Embodiment 3

[0038] (1) Preparation of 4,4'-dihydroxy-α-hiseric acid

[0039] Taking p-hydroxycinnamic acid and diisopropylethylamine as reactants, adding the solvent to acetonitrile, the ratio of p-hydroxycinnamic acid, diisopropylethylamine and solvent by weight is 1:3:15, and then 5% photocatalyst [Ru(bpy) 3 ]Cl 2 Stir evenly, then irradiate with visible light for 10 hours to obtain the crude product, and then recrystallize to obtain the product 4,4'-dihydroxy-α-hiseric acid.

[0040] White crystal, Mp>300℃.Anal.Calcd for C 18 h 16 o 6 :C,65.85%;H,4.91%.Found:C,65.76%;H,4.93%.Positive FAB-MS

[0041] m / z:329[M+H] + . 1 H-NMR (DMSO-d6)d: 3.65 (2H, m), 4.14 (2H, m), 6.70 (4H, d, J = 8.8Hz), 7.12 (4H, d, J = 8.8Hz).

[0042] (2) Preparation of Abrusamide

[0043] 4,4'-dihydroxy-α-hiseric acid and tyrosine obtained in step (1), 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride, three Ethylamine, 4-dimethylaminopyridine and dichloromethane are mixed according to the molar ...

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Abstract

The invention discloses a preparation method of abrus mollis Abrusamide. The method includes the steps that p-hydroxy-cinnamic acid is adopted as a raw material, a ring-closure reaction is carried out under visible light catalysis, a compound 4,4'-dyhydroxy-alpha-truxillic acid is obtained, then the compound 4,4'-dyhydroxy-alpha-truxillic acid and tyrosine are subjected to an amidation reaction, and abrus mollis Abrusamide can be obtained. Chemical synthesis of abrus mollis Abrusamide is achieved, the raw material source is rich, the price is low, the reaction is environmentally friendly and low in cost, and the yield is high.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry. It particularly relates to a preparation method of Abrusamide. Background technique [0002] Chicken bone grass is a commonly used traditional Chinese medicine. It has the effects of clearing away heat and detoxification, reducing dampness and jaundice, soothing the liver and relieving pain, especially for liver and gallbladder diseases. Chicken bone grass was first discovered in Baiyun Mountain, Guangzhou, so it is also called Guangzhou Acacia, aliased with tile yellow head grass, rhubarb grass, false cow licorice, red hen grass, etc. At present, there are two kinds of chicken bone grass used as traditional Chinese medicine, one is chicken bone grass, that is, Acacia guangzhou; The main raw material is often used as a substitute for chicken bone grass in Guangdong and Guangxi. Studies have shown that chicken bone grass has a good liver protection effect, mainly to protect against ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C235/40C07C231/02
CPCC07C51/353C07C231/02C07C235/40C07C62/32
Inventor 朱华申利群苏健李丹妮宋雅玲牛思琪戴忠华
Owner GUANGXI UNIV OF CHINESE MEDICINE