Method for synthesizing sophocarpine

A synthesis method and technology of sophocarpine can be applied in the direction of organic chemistry, etc., and can solve the problems such as difficulty in purifying sophocarpine

Active Publication Date: 2015-04-29
NANKAI UNIV
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Problems solved by technology

The separation and purification technology of matrine is ve...

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  • Method for synthesizing sophocarpine
  • Method for synthesizing sophocarpine
  • Method for synthesizing sophocarpine

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Embodiment Construction

[0007] Synthesis of 14-phenylthiomatrine:

[0008]

[0009] Add 70 mL of tetrahydrofuran into a 250 mL four-neck flask, and lower the temperature to -78°C under the protection of argon. Add 5.0mL (35.6mmol) diisopropylamine and 16.1mL (38.9mmol) n-hexane solution (2.4mol / L) of n-butyllithium to the flask, stir for 15min, then add 4.0g (16.1mmol) Sophora flavescens to the flask Alkali and 3.6g (16.4mmol) diphenyl disulfide tetrahydrofuran solution (30mL), warmed up to room temperature, after stirring for 2h, add 50mL saturated sodium carbonate solution to the system, separate the liquids, the water phase is thoroughly washed with ethyl acetate several times. Extract, combine the organic phases, wash with saturated brine, dry over anhydrous sodium sulfate, remove the solvent, and separate by silica gel column chromatography to obtain 5.5 g of yellow liquid. Yield: 95.8%. 1 H NMR (400MHz, CDCl 3 )δ7.56-7.47(m, 2H), 7.32-7.22(m, 3H), 4.39(dd, J=12.8, 4.4Hz, 1H), 3.91-3.76(m,...

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Abstract

The invention provides a new method for synthesizing sophocarpine. The method comprises the following steps: removing alpha-position hydrogen in amide in matrine by taking matrine as a raw material and taking lithium diisopropylamide (LDA) as alkali, then directly performing nucleophilic substitution reaction with diphenyl disulfide to obtain 14-thiophenyl matrine, oxidizing by IBX (o-iodyl-benzoic acid) in a water phase to obtain 14-phenylsulfinyl matrine and eliminating benzenesulfenic acid under the assistance of weak alkali to obtain sophocarpine. The method provided by the invention takes the step of oxidizing a nitrogen-containing thioether compound with IBX in a water phase to form sulfoxide as the key step for synthesizing sophocarpine. The method is characterized by high efficiency, environmental friendliness and easiness in operation. The synthesis route is as shown in the description.

Description

technical field [0001] The invention relates to a new synthesis method of sophocarpine and a key step in the synthesis process: oxidizing nitrogen-containing sulfide into sulfoxide with o-iodobenzoic acid (IBX) in the water phase. Background technique [0002] Matrine alkaloids are represented by matrine, oxymatrine, and sophocarpine, a class of alkaloids with similar chemical structures. Widely present in the leguminous Sophora genus such as Sophora flavescens, Sophora flavescens and other plants. It is the main active ingredient of several commonly used Chinese herbal medicines. It has the effects of clearing away heat, drying dampness, killing insects, and diuresis. It has a wide range of functions and obvious effects. Sophocarpine has obvious anti-Coxsackie B virus effect and immune regulation function. In the screening of the anti-SARS virus activity by the National New Drug Screening and Research Center entrusted by Renji Hospital, it was found that sophocarpine has ...

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Application Information

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IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 汪清民李朝杰刘玉秀
Owner NANKAI UNIV
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