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Preparation method for physostigmine precursor compound

A precursor compound, physostigmine technology, applied in the direction of organic chemistry, can solve the problems of unfavorable industrial production, long synthesis steps, high equipment requirements, etc., and achieve the effect of high feasibility of industrial production, convenient operation and low environmental pollution

Inactive Publication Date: 2017-09-05
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The technical synthesis steps of Chinese patent CN 101121717 A are longer (8 steps), and the total yield is lower (less than 20%). Metal sodium, etc. are used in the synthesis many times, and the requirements for equipment are high, which is not conducive to industrial production.

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  • Preparation method for physostigmine precursor compound
  • Preparation method for physostigmine precursor compound
  • Preparation method for physostigmine precursor compound

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Embodiment Construction

[0032] The preparation method of the physostigmine precursor compound of the embodiment of the present invention is given below.

[0033] step one

[0034]

[0035] Amino group protection step reaction formula

[0036] Dissolve 5-methoxytryptamine (19g, 100mmol) and 4-N,N-dimethylaminopyridine (DMAP, 1.22g, 10mmol) in acetonitrile (400mL), then add triethylamine (30.3g, 300mmol). After the reactant was stirred at room temperature for 1h, it was lowered to 0°C, then a solution of benzyl chloroformate (CbzCl, 35.8g, 210mmol) in acetonitrile (10mL) was slowly added, then raised to room temperature and stirred for 12h, and saturated chlorine was added after the reaction of the raw materials was complete. Quenched with ammonium chloride solution (100 mL), concentrated under reduced pressure to remove the acetonitrile solvent, then diluted with water (300 mL), extracted the aqueous phase with ethyl acetate (100 mL × 3), combined the organic phases, washed the organic phase with...

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Abstract

The invention relates to physostigmine and provides a preparation method for a physostigmine precursor compound. The physostigmine precursor compound is prepared with 5-methoxytryptamine as a starting raw material through amino protection, intramolecular cyclization, methylation and amide reduction. The preparation method has the advantages of simple synthesis route, usage of cheap and easily available synthesis reagents, simple synthesis operation, friendliness to environment and the like and is highly feasible in industrial production. In particular, a cyclization reagent, i.e., 1,3-dichloro-5,5-dimethylhydantoin, used in the key intramolecular cyclization is a commercial germicide and disinfectant and is cheap, easily available and friendly to environment. The physostigmine precursor compound used as a synthesis precursor or intermediate for physostigmine is also applicable as a synthesis precursor for phenserine and a variety of physostigmine derivatives and thus has good application value and development potential.

Description

technical field [0001] The invention relates to physostigmine, in particular to a preparation method of a physostigmine precursor compound. Background technique [0002] Physostigmine (Phsostigmine) is a natural alkaloid, its structural formula is: [0003] [0004] It mainly exists in the seeds of a leguminous plant called poisonous lentils in West Africa. It was first extracted from the seeds of poisonous lentils (Physostigma venenosum) in 1864 by scientists J. Jobs and O. Hesse. Studies have shown that it has excellent inhibitory activity on acetylcholinesterase (acetylcholinesterase, AChE), so it was first used by scientists in anticholinesterase therapy (Greig NH, Pei XF, Soncrant TT, Ingram DK, BrossiA.Med.Res . Rev. 1995, 15, 3). In addition, in view of its excellent biological activity, physostigmine is also widely used in the treatment of diseases such as glaucoma and senile dementia (Axelsson U.Acta Ophthalmol.1969,47,1057; Mohs RC, Davis B, Johns CA, Mathe AA...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 罗世翊刘晨然张诗燊邵文尧卢英华滕飞雪
Owner XIAMEN UNIV
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