Gastrodin ferulate compound and preparation method and application of gastrodin ferulate compound

A technology of ester compound and ferulic acid ester, which is applied in the field of medicine and chemical industry

Inactive Publication Date: 2014-12-24
SHANGHAI MODERN HASEN SHANGQIU PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] At present, there is no public report that combining gastrodin ferulic acid into a lipid compound is used to improve and treat neurasthenia, neurasthenia syndrome and angioneurotic headache

Method used

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  • Gastrodin ferulate compound and preparation method and application of gastrodin ferulate compound
  • Gastrodin ferulate compound and preparation method and application of gastrodin ferulate compound
  • Gastrodin ferulate compound and preparation method and application of gastrodin ferulate compound

Examples

Experimental program
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Effect test

Embodiment 1

[0087] A gastrodin ferulic acid ester compound, the preparation of the compound shown in the formula (II) is realized by the following steps:

[0088] (1) At 32°C, add anhydrous glucose to the catalyst perchloric acid and acetylate it with acetic anhydride to generate full acetyl sugar. TLC detects the end point of the reaction. After the acetylation is completed, hydrogen bromide (gas) is introduced, and the temperature is controlled at At 28°C, hemiacetal hydroxy bromide of peracetyl sugar is used to synthesize bromotetraacetylglucose, and the molar ratio of feed is anhydrous glucose: acetic anhydride: perchloric acid: hydrogen bromide = 1: 7.5: 0.04: 0.76;

[0089] (2) Add phase transfer catalyst tetrabutylammonium bromide, carbonate and p-hydroxybenzaldehyde in the two-phase system composed of chloroform and water with a volume ratio of 1:1, control the temperature at 55°C, bromotetraacetylglucose Dissolve in chloroform and add dropwise. The weight ratio of bromotetraacety...

Embodiment 2

[0095] In the specific implementation of the present invention, a gastrodin ferulic acid ester compound, said gastrodin ferulic acid ester compound is a compound shown in formula (I), and its preparation method is:

[0096] Preparation of compounds of formula (Ic)

[0097] Acetylgastrodin 4.6g (i.e. 10.13mmol), pyridine 1.2g (i.e. 15.20mmol), DMAP0.4g (i.e. 3.04mmol) and 100ml dichloromethane shown in formula (II) are dropped into the reactor, stirred, and another Acetyl feruloyl chloride 3.9g (i.e. 15.20mmol) shown in formula (III) was dissolved in 100ml methylene chloride, then the acetyl feruloyl chloride methylene chloride solution was dripped into the reactor, stirred at room temperature for 2 hours, and then the Wash with 3% hydrochloric acid and saturated ammonium chloride solution, dry over anhydrous magnesium sulfate, filter, evaporate the solvent under reduced pressure to obtain the compound (5.9 g, 93%) shown in formula (Ic), 1 H NMR (400MHz, CDCl 3 )δ7.66(d, J=16...

Embodiment 3

[0103] A kind of gastrodin ferulic acid ester compound of the present invention, described this compound is the compound shown in formula (1b), and its preparation method is:

[0104] Put 2.0g (2.97mmol) of the compound represented by formula (Ic) into 40ml of diethylamine, stir at 60°C, wait until the dissolution is complete, add 40ml of toluene to dilute, then wash with 1M sulfuric acid and saturated ammonium chloride, and anhydrous sulfuric acid Sodium drying, filtering, steaming toluene, chromatographic silica gel column ethyl acetate-petroleum ether volume ratio 1: 1 mixed together as mobile phase, isolated compound 428mg shown in formula (Ib), 1 H NMR (400MHz, DMSO) δ9.60(s, 1H), 7.57(d, J=15.9Hz, 1H), 7.41–7.28(m, 3H), 7.12(d, J=8.2Hz, 1H), 7.04 (d, J=8.5Hz, 2H), 6.79(d, J=8.2Hz, 1H), 6.51(d, J=15.9Hz, 1H), 5.31(d, J=4.7Hz, 1H), 5.14(s ,2H),5.08(d,J=4.4Hz,1H),5.02(d,J=5.2Hz,1H),4.88(d,J=7.2Hz,1H),4.55(t,J=5.7Hz,1H ),3.81(s,3H),3.78–3.62(m,1H),3.46(dt,J=11.8,6.0Hz,1H),...

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Abstract

The invention relates to a gastrodin ferulate compound and a preparation method and application of the gastrodin ferulate compound. The problem that gastrodin and ferulic acid are prepared into the gastrodin ferulate compound and the problem of preparation of medicine for improving and treating neurasthenia, neurasthenia syndrome and angioneurotic headache are effectively solved. The method comprises the following steps: carrying out acetylization on anhydrous dextrose by using acetic anhydride; carrying out hemiacetal hydroxyl bromination, and then condensing with p-hydroxy benzaldehyde; carrying out hydride reduction to obtain acegastrodine; carrying out hydroxyl acetylated protection on ferulic acid to obtain 3-(4'-acetyl-3'-methoxyphenyl)-2-acrylic acid, and then preparing cetylferuloyl chloride; dissolving acegastrodine into a drying solvent and adding a nucleophilic acylation catalyst and an acid-binding agent; dissolving cetylferuloyl chloride into the drying solvent; mixing the two sollutions to obtain an ester compound; and carrying out deacetylation under an alkaline condition, thus obtaining the gastrodin ferulate compound. The gastrodin ferulate compound disclosed by the invention has the efficacies of calming mind, mesmerizing, and improving blood circulation of the brain.

Description

technical field [0001] The invention relates to the field of medicine and chemical industry, in particular to a gastrodin ferulic acid ester compound and its preparation method and application. Background technique [0002] The English name of sedative-hypnotic drugs is sedative-hypnotic, and normal use of sedative-hypnotic drugs is beneficial to human health. Sedative-hypnotics help prevent insomnia from impairing human health and normal life. Sedative hypnotics are good medicines that effectively help sleep and effectively improve sleep. Sedative-hypnotics can avoid the serious harm of insomnia to the human body, sedative-hypnotics can treat insomnia, and sedative-hypnotics can improve sleep quality. Most sedative and hypnotics belong to health drugs, not psychotropic drugs. There is no sharp boundary between sedatives and hypnotics, only the difference in quantity. Small doses of hypnotics have a sedative effect. Sedatives make people quiet. Appropriate use of sedat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00A61K31/7034A61P25/20A61P25/00A61P25/06
Inventor 刁文瑞陈洪江正祥李新柱于秀华刘统斌
Owner SHANGHAI MODERN HASEN SHANGQIU PHARMA
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