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Chemical synthesis method of laetispicine

A technology of quincetin and chemical synthesis, which can be applied in the fields of organic chemistry, drug combination, nervous system diseases, etc., and can solve the problems of unfavorable structural modification research and low content of quincetin.

Inactive Publication Date: 2013-02-27
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the content of phytocarpine in nature is low, and the extraction rate is about 3 / 10,000, and there is no report on its chemical synthesis
These are not conducive to its further structural transformation and other research

Method used

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  • Chemical synthesis method of laetispicine
  • Chemical synthesis method of laetispicine
  • Chemical synthesis method of laetispicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 The preparation of 3,4-methylenedioxyphenyl glycidic acid methyl ester (2)

[0035] Dissolve 6.0g (40mmol) of piperonal (1) and 4.6ml (60mmol) of methyl chloroformate in 15ml of absolute methanol, slowly drop into 5ml of absolute methanol containing 6.5g (60mmol) of sodium methoxide in an ice-salt bath under the protection of argon solution, the dropwise addition time was about 10 minutes, and after the dropwise addition was completed, it was stirred in an ice-salt bath for 1 hour. Add a mixed solution of 20ml water and 20ml diethyl ether to the reaction solution, stir in an ice bath for 1h, a large amount of solids are generated, filter with suction, wash with diethyl ether, and dry to obtain white solid 3,4-methylenedioxyphenylmethyl glycidate (2 ) 7.8g, crude product yield 88%, directly carry out next step reaction. Wherein, the methyl chloroformate and sodium methoxide can also be replaced by ethyl chloroacetate and sodium ethoxide, and the reaction solve...

Embodiment 2

[0037] Example 2 Preparation of 3,4-methylenedioxyphenylacetaldehyde (4)

[0038]Dissolve 14.0g of sodium methoxide in 100ml of absolute methanol, slowly drop into 56.6g (0.25mol) (2) of 50ml of anhydrous toluene solution under the protection of argon in an ice bath, stir in an ice bath for 30 minutes, add 6ml of water and 200ml of Diethyl ether was stirred in an ice bath for 2 hours, a large amount of solids were produced, suction filtered, washed with anhydrous ether, and dried to obtain 64.9 g of crude sodium 3,4-methylenedioxyphenyl glycidic acid, which was directly carried out to the next reaction without further treatment.

[0039] Dissolve 64.9g (0.28mol) of crude product 3,4-methylenedioxyphenyl glycidic acid sodium and 16.2ml (0.28mol) of glacial acetic acid in 50ml of anhydrous toluene solution, heat and reflux for 2.5 hours (a large amount of CO 2 After cooling, the organic phase was washed twice with 2×50 ml of water, dried over anhydrous sodium sulfate, filtered, ...

Embodiment 3

[0041] Example 3 Preparation of 3,4-methylenedioxyphenethyl alcohol (5)

[0042] Under ice-cooling, dissolve 0.30g (1.8mmol) (4) in 15ml of anhydrous methanol, slowly add dropwise a solution of 0.09g (2.2mmol) sodium borohydride in 5ml of anhydrous methanol, and stir in ice-bath for 15 minutes. Add 20ml of water and 20ml of dichloromethane, wash the aqueous phase twice with 2×20ml of dichloromethane, combine the organic phases, dry over anhydrous sodium sulfate, filter, and evaporate the solvent to obtain a colorless oily substance 3,4-methylenedioxy Phenylethyl alcohol (5) 0.28g, yield 93%. Proceed directly to the next reaction.

[0043] 1 H-NMR (CDCl 3 , 300MHz) δ: 2.79 (t, 2H), 3.83 (t, 3H), 5.94 (s, 2H), 6.67-6.78 (m, 3H).

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Abstract

A sulphonyl tetrazole compound 7 with the following structure, its preparation method and its use for preparing laetispicine. The said sulphonyl tetrazole compound 7, (1-phenyl-5-(3,4-methylenedioxyphenyl ethyl) sulphonyl tetrazole), is obtained from piperonal as raw material and by steps of Darzens condensation, hydrolysis, decarboxylation, reduction, condensation and oxidation. Laetispicine is prepared from the said compound as raw material, by condensation with 9-carbonyl-2E-4E-nonadienoic acid isobutyramide (compound 14), or by reaction with 5-(tetrahydropyran-2-oxo) n-pentanal (compound 10), deprotection, Swern oxidation, Wittig-Horner reaction, hydrolysis and amidation. As shown in H NMR, C NMR, MS and IR, the laetispicine prepared from the above-said compound is consistent with the laetispicine extracted from natural products.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a chemical synthesis method of a natural product, phytocarpine. Background technique [0002] Depression is a common mental illness, and patients account for about 3% to 5% of the world's total population. According to the report of the World Health Organization (WHO), depression has become the fourth largest disease in the world, and it is estimated that by 2020, the functional disability caused by severe depression will be second only to ischemic heart disease. [0003] At present, the exact etiology and pathological mechanism of depression are still not very clear. DA), acetylcholine, γ-aminobutyric acid and other levels decreased. So far, a series of antidepressants such as MAOIs, SSRI, NARI, SNRI, etc. have been developed. However, the existing antidepressants all have a lag period in their onset of action, and only 50% to 65% of patients obtain significa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/60A61P25/24
CPCC07D405/12C07D317/60A61P25/24
Inventor 沈竞康姚舒译潘胜利胡定宇钱伏刚么春艳王昕
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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