Method for preparing coptisine from coptis mixed alkaloid based on common basic structural characteristic

A basic structure and alkaloid technology, applied in the direction of organic chemistry, can solve the problems of easily forming only one ring-closing product, removing one aldehyde group by-product, and many steps in the total synthesis of coptisine, so as to save purification The effect of steps, strong activity, and simple and easy-to-operate preparation method

Inactive Publication Date: 2011-03-16
CHANGCHUN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Shuai Chen [2] etc. used 2,3-dimethoxybenzaldehyde as the starting material, and synthesized coptisine hydrochloride through 5 steps of demethylation, cyclization, condensation and ring closure, with a total yield of 9.9%, but due to 2,3- Dimethoxybenzaldehyde is under the HBr of 48%, when making through high-temperature demethylation, reaction time is too short or temperature is too low all to easily generate the by-product that

Method used

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  • Method for preparing coptisine from coptis mixed alkaloid based on common basic structural characteristic
  • Method for preparing coptisine from coptis mixed alkaloid based on common basic structural characteristic
  • Method for preparing coptisine from coptis mixed alkaloid based on common basic structural characteristic

Examples

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Effect test

Embodiment 1

[0047] Example 1: Preparation of mixed alkaloids from Tetrahydrocoptis Rhizoma

[0048] Weigh 1 g of Coptis rhizome mixed alkaloids into a 100ml three-necked bottle, add 25ml of ethanol aqueous solution with a mass fraction of 70% ethanol, heat and dissolve to reflux at 80°C, the concentration of Coptis rhizome mixed alkaloids in ethanol aqueous solution is 0.04g / mL, add no Potassium carbonate water 1.6g, the mass ratio of anhydrous potassium carbonate and Coptidis rhizome mixed alkaloid is 1.6: 1, then every 5min is divided into three equal amounts and adds the sodium borohydride that total amount is 0.12g and reacts, and described sodium borohydride The mass ratio of mixed alkaloids with Coptidis rhizome was 0.12:1. After stirring and reacting at room temperature for 4 hours, suction filtration was performed to filter out the insoluble matter, which was recrystallized from benzene to obtain 0.83 g of mixed alkaloids of Coptidis rhizome with a yield of 84%.

Embodiment 2

[0049] Example 2: Preparation of mixed alkaloids of Tetrahydrocoptis Rhizoma

[0050] Weigh 1 g of the mixed alkaloids of Coptis chinensis into a 100 ml three-necked bottle, add 40 ml of ethanol aqueous solution with a mass fraction of 80% ethanol, heat and dissolve to reflux at 80°C, the concentration of the mixed alkaloids of Coptis chinensis in the aqueous ethanol solution is 0.025 g / mL, add Potassium carbonate water 3g, the mass ratio of anhydrous potassium carbonate and Coptidis rhizome mixed alkaloids is 3: 1, divides three times every interval 5min equal amount and adds the sodium borohydride that total amount is 0.3g to react, described sodium borohydride The mass ratio of mixed alkaloids with Coptidis rhizome was 0.3:1, stirred and reacted at room temperature for 6 hours, then suction filtered to filter out insoluble matter, which was recrystallized from benzene to obtain 0.88 g of mixed alkaloids of Coptidis rhizome with a yield of 87%.

Embodiment 3

[0051] Example 3: Preparation of mixed alkaloids from Tetrahydrocoptis Rhizoma

[0052] Weigh 1g of the mixed alkaloids of Coptidis rhizome in a 100ml three-neck bottle, add 50ml of ethanol aqueous solution with a mass fraction of 90% ethanol, heat and dissolve the mixed alkaloids of Coptidis rhizome with aqueous ethanol to reflux at 80°C, and the mixed alkaloids of Coptidis rhizome in the aqueous ethanol solution The concentration is 0.02g / mL, add 4g of anhydrous potassium carbonate, the mass ratio of anhydrous potassium carbonate and Coptidis rhizome mixed alkaloids is 4:1, then add a total of 0.6g of sodium borohydride in equal amounts three times at intervals of 5min Carry out the reaction, the mass ratio of sodium borohydride and Coptidis rhizome mixed alkaloids is 0.6:1, stir and react at room temperature for 8 hours, after the reaction is completed, filter with suction, filter out the insoluble matter, and recrystallize the insoluble matter through benzene to obtain Tetr...

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Abstract

The invention discloses a method for preparing coptisine from coptis mixed alkaloid based on common basic structural characteristic. The coptisine is synthesized by using the coptis mixed alkaloid consisting of berberine, coptisine, palmatine and jateorhizine which have the same isoquinoline ring structure, and by performing reductive hydrogenation, hydroxylation of methoxy group and methylenedioxy group, cyclization of ortho-oxhydryl group and oxidative hydrogenation, wherein the total yield can reach 16 percent. Compared with the conventional method for preparing the coptisine, the method is simple and convenient, and easy to operate and eliminates the purification step of the raw material during the synthesis of medicaments. By the method, the rough mixed total alkali with indefinite medicinal effect dispersion and low purity is converted into monomer coptisine with high antibacterial specificity and activity. The method is easy and convenient to operate, low in cost and wide in application prospect, is suitable for batch production of the coptisine, can provide reference idea for research on conversion of main components of other Chinese herbal medicines which have similar structures, and has great guidance significance for the improvement on the utilization value of the traditional Chinese medicine and the development and preparation of new medicaments.

Description

technical field [0001] The invention relates to a method for preparing coptisine based on the mixed alkaloids of Coptidis Rhizoma with common basic structural characteristics. Background technique [0002] Coptidis mixed alkaloids are extracted from Chinese medicine Coptis chinensis, with the same isoquinoline ring as the main structure, and methoxy, methylenedioxy, and hydroxyl are substituted at 2, 3, 9, and 10 positions. These include palmatine and jatrorrhizine, berberine, and coptisine. Among them, berberine is the most widely studied and applied. Coptisine, which has multiple pharmacological effects such as hypoglycemic, anti-tumor, immune regulation, antibacterial and anti-inflammatory, and cardiovascular improvement, has limited its further research and application because of its extremely low content in Coptis chinensis. Coptisine is light yellow needle crystal in ethanol, very slightly soluble in water, slightly soluble in ethanol, soluble in alkali. It has been...

Claims

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Application Information

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IPC IPC(8): C07D455/03
Inventor 王道武庞雪张龙
Owner CHANGCHUN UNIV OF TECH
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