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

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...

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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 takes off a methyl group, in addition temperature is too high in the process of closing If the temperature is too low, only one ring-closing product will be formed. If the temperature is too high, a by-product that removes an aldehyde group will be easily formed. The temperature is difficult to control. Therefore, there are many steps in the total synthesis of coptisine, and the yield is low, which only has theoretical significance.

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