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Preparation method of full-aromaticity beta-carboline compound

An aromatic and carboline technology, applied in the field of medicine, can solve the problems of high cost, small number of products, and limitations of scientific research and production applications

Inactive Publication Date: 2013-05-22
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Most of the methods for obtaining β-carboline alkaloids are separated by plant extraction (for example, from the rhizome of Yin Bupleurum). The number of products obtained by this method is small and the cost is high, which greatly limits its scientific research and production applications

Method used

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  • Preparation method of full-aromaticity beta-carboline compound
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  • Preparation method of full-aromaticity beta-carboline compound

Examples

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Embodiment 1

[0023] Preparation of tryptophan methyl ester hydrochloride

[0024] Dissolve 2.00 mmol of tryptophan in 10 ml of anhydrous methanol, add 20 ml of thionyl chloride at low temperature to catalyze, reflux reaction at 65-70 °C, check the progress of the reaction by TLC, and the reaction is complete after about 4-5 hours. Methanol was distilled off, and the product was recrystallized with absolute ethanol to obtain 460 mg of white crystals with a yield of 95%. EIMS: 218(M + ), 130 (M + -88), 159 (M + -59).

Embodiment 2

[0026] Preparation of 2-Acetoxypropionyl Chloride

[0027] Mix 30mmol α-hydroxypropionic acid and 90mmol acetic anhydride in a 50 ml round bottom flask, and stir at room temperature or low temperature. After 30 minutes, add 3ml of purified water and a catalytic amount of concentrated hydrochloric acid to the reaction solution, stir at room temperature or at low temperature, and suspend the reaction after about 30 minutes. Extract the reaction liquid with 1,2-dichloroethane, add 45 mmol of thionyl chloride, reflux reaction for 3-4 hours, distill off 1,2-dichloroethane for later use, the yield is about 90%.

Embodiment 3

[0029] Preparation of 1-(1'-acetoxyethyl)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid methyl ester

[0030] Use a 25ml round bottom flask to replace the inert gas with a double-row tube, dissolve 1.80mmol of tryptophan methyl ester hydrochloride in 10ml of anhydrous 1,2-dichloroethane, inject it with a syringe, and then add triethyl Add 5.4 mmol of amine, 1.80 mmol of 2-acetoxypropionyl chloride, and react at 0°C for 2 hours. Add 186 mml of phosphorus oxychloride to the reaction system, and heat to reflux for 10-12 hours. It was then concentrated and separated by column chromatography to obtain 0.35 g of a colorless oily liquid with a yield of 61%. EIMS: 314(M + ), 255 (M + -59), 196 (M + -118), 168 (M + -146), 147 (M + -167), 122 (M + -192), 59 (M + -255).

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Abstract

The invention discloses a preparation method of a full-aromaticity beta-carboline alkaloid compound with the structure in a general formula I and a general formula II and pharmaceutically acceptable compounds and salts thereof (including stereisomers or variable isomers). The full- aromaticity beta-carboline alkaloid compound disclosed by the invention has good anti-allergic activity and can be used for treating diseases such as influenza with fever, alternate attacks of chill and fever, malaria and stagnation of liver-qi.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to a preparation method of fully aromatic β-carboline compounds. Background technique [0002] β-carboline alkaloids are a large class of alkaloids from natural sources, which are widely distributed in nature. These compounds have broad-spectrum biological activities and important pharmacological activities. β-carboline derivatives have various biological activities such as affecting the central nervous system, anti-cancer, anti-tumor, anti-platelet aggregation, anti-virus, anti-parasite, and inhibition of phosphodiesterase. [0003] Most of the methods for obtaining β-carboline alkaloids are separated by plant extraction (for example, from the rhizome of Yinbupleurum). The number of products obtained by this method is small and the cost is high, which greatly limits its scientific research and production applications. Therefore, the synthesis of such compounds has become a resear...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCY02A50/30
Inventor 贾鹏飞刘占荣何敬宇王娟苌美燕司海燕王颖
Owner SHIJIAZHUANG UNIVERSITY