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Marine natural product Echinoclathrine A preparation method

A natural product, marine technology, applied in the field of medicine and chemical industry, can solve the problems of complex extraction process and unfavorable industrial production, and achieve the effects of simple process, favorable for large-scale production, and improved efficiency and yield

Active Publication Date: 2013-10-16
LINHAI LIANSHENG CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the corresponding product can be obtained by using the extraction method, the extraction process is complicated and is not conducive to industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment １

[0036] Add 420mg (2.2mmol) of n-capric acid and 6mL chloroform in the flask, add thionyl chloride 1.05g (8.8mmol) and 0.145gDMF at room temperature, heat up to reflux, stop the reaction after reacting for 4h, remove the solvent and excess Thionyl chloride can be used to obtain n-caproyl chloride. Then, add m-chloro-o-aminophenol 215mg (1.5mmol) and 10ml chloroform in another flask, and slowly add the above-mentioned n-caproyl chloride solution diluted with 10mL chloroform under ice-bath conditions, after the dropwise addition, slowly add Use 10mL of chloroform and diluted triethylamine 222mg (2.2mmol) solution, after the dropwise addition, stir under ice bath conditions to carry out the substitution reaction for 2h, stop the reaction, wash 3 times with 25mL of sodium chloride aqueous solution, separate the organic phase, Evaporate to dryness with a rotary evaporator, and purify by column (using petroleum ether / ethyl acetate as mobile phase, the volume ratio of petroleum ether ...

Embodiment ２

[0039] Add 420mg (2.2mmol) of n-capric acid and 6mL chloroform in the flask, add thionyl chloride 1.05g (8.8mmol) and 0.145gDMF at room temperature, heat up to reflux, stop the reaction after reacting for 4h, remove the solvent and excess Thionyl chloride can be used to obtain n-caproyl chloride. Then, add m-chloro-o-aminophenol 215mg (1.5mmol) and 10ml chloroform in another flask, and slowly add the above-mentioned n-caproyl chloride solution diluted with 10mL chloroform under ice-bath conditions, after the dropwise addition, slowly add Use 10mL of chloroform and diluted pyrrole 2.2mmol solution, after the dropwise addition, control the temperature and stir at 0°C to carry out the substitution reaction for 3h, stop the reaction, wash 3 times with 25mL of sodium chloride aqueous solution, separate the organic phase, and use Evaporate to dryness with a rotary evaporator, pass through a column (using petroleum ether / ethyl acetate as the mobile phase, and the volume ratio of petr...

Embodiment ３

[0042] Add 215 mg (1.5 mmol) of m-chloro-o-aminophenol and 10 ml of chloroform into the flask, and slowly add 213 mg (2.0 mmol) of n-caproyl chloride diluted with 10 mL of chloroform dropwise under ice-bath conditions. Add 10 mL of chloroform and diluted morpholine 2.2 mmol solution. After the dropwise addition, control the temperature and stir at -5°C to carry out the substitution reaction for 2.5 h, stop the reaction, wash 3 times with 25 mL of sodium chloride aqueous solution, separate The organic phase was evaporated to dryness with a rotary evaporator, and purified by column (petroleum ether / ethyl acetate as mobile phase, the volume ratio of petroleum ether to ethyl acetate was 50:1) to obtain the compound of formula III, which was converted to m-chloro-o- Aminophenol is a benchmark, and the molar yield is 85%.

[0043]Get formula IV compound 2-methyl 4-pyridine boronic acid 30.8mg (0.22 mmol), the formula III compound 31mg (0.1 mmol) that above-mentioned method obtains, ...

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PUM

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Abstract

The invention relates to a marine natural product Echinoclathrine A preparation method and belongs to the technical field of pharmaceutical chemicals. In order to solve the problems that the existing technology is simple and low in yield, the invention provides the marine natural product Echinoclathrine A preparation method. The preparation method comprises the following steps: with an acid application agent, 3-cl-2-aminophenol and n-butyryl chloride butanoyl chloride perform a substitution reaction in halogenated hydrocarbon to acquire an intermediate product; under the function of an alkaline reagent, with a palladium catalyst and a phosphorus compound, the intermediate product and 2-methyl pyridine boric acid have a reaction to acquire the final product Echinoclathrine A. The preparation method has the advantages of simple technology, and high product purity and yield.

Description

technical field [0001] The invention relates to a preparation method of marine natural product Echinoclathrine A, which belongs to the technical field of medicine and chemical industry. Background technique [0002] Most pyridine alkaloids are of marine origin, either concise polycyclic aromatic-based pyrido or 3-alkylpyridines, such as those isolated from sponge or ascidian metabolites. At present, it is found that Echinoclathrine A, a pyridine alkaloid isolated from marine organisms, is a compound with 4-aryl-2-picoline as a common structural unit. The structural formula of this compound is as follows: [0003] [0004] Because this compound has certain biological activity, therefore, has better development prospect, but, existing mostly is to obtain from the separation such as marine metabolism, as disclosed Echinoclathrines A-C among Atsushi Kitamura etal.Tetrahedron55 (1999) 2487-2492: A New Class of Pyridine Alkaloids from an Okinawan Sponge, Echinoclathria sp repo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/40
Inventor 周其忠张斌陈仁尔蒋华江俞小鸥
Owner LINHAI LIANSHENG CHEM