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α-Asarocyl alcohol and its preparation method and application

A technology of asaranol and fatty alcohol, applied in the field of preparation of alpha-asaranol, can solve problems such as cognitive dysfunction, severe allergic reaction and the like

Active Publication Date: 2016-11-02
NORTHWEST UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the second-generation antiepileptic drugs have partially improved the shortcomings of the first-generation drugs, most of the second-generation drugs can still be accompanied by some specific adverse reactions, such as cognitive dysfunction, acute eye symptoms, severe allergic reactions, etc.

Method used

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  • α-Asarocyl alcohol and its preparation method and application
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  • α-Asarocyl alcohol and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of Methyl 2,4,5-Trimethoxycinnamate

[0022] A 3L three-necked flask with a thermometer and a condenser tube was added with 195.5g (1.35mol) of McFarlandic acid (1.35mol), methanol (50mL) and toluene (750mL), heated to reflux at 110°C for 4 hours, cooled to room temperature, and then added with 2,4 , 196.2g (1.0mol) of 5-trimethoxybenzaldehyde, 134.5g (1.7mol) of pyridine, and 14.5g (0.17mol) of piperidine, heated to reflux for 18 hours, concentrated under reduced pressure, then added ethyl acetate (200mL), Water (200mL), extracted and separated 3 times, combined the organic phases, concentrated under reduced pressure, added ethanol (1000mL), refrigerated overnight in the refrigerator, after the precipitation was precipitated, filtered with suction, washed 3 times with 500mL of ice ethanol to obtain a light yellow solid 166.3 g, 66% yield.

[0023] m / z=[M+1]253.1086

[0024] 1 H NMR (600MHz, cdcl3) δ7.97(d, J=16.1Hz, 1H), 7.01(s, 1H), 6.50(s, 1H), 6.38(d,...

Embodiment 2

[0027] Preparation of ethyl 2,4,5-trimethoxycinnamate

[0028] In a 250mL three-neck flask with a thermometer and a condenser tube, add 20.2g (0.14mol) of McFarlandic acid (0.14mol), ethanol (10mL), and toluene (150mL) respectively, heat and reflux at 110°C for 4 hours, cool to room temperature, and then add 2,4 , 19.6g (0.1mol) of 5-trimethoxybenzaldehyde, 13.5g (0.17mol) of pyridine, and 1.5g (0.017mol) of piperidine, heated to reflux for 18 hours, concentrated under reduced pressure, then added ethyl acetate (50mL), Water (50mL), extracted and separated 3 times, combined the organic phases, concentrated under reduced pressure, added ethanol (150mL), refrigerated overnight, after the precipitate was precipitated, filtered with suction, washed 3 times with 100mL ice-ethanol to obtain a light yellow solid 16.0 g, 60% yield.

Embodiment 3

[0030] Preparation of Propyl 2,4,5-Trimethoxycinnamate

[0031] In a 250mL three-neck flask with a thermometer and a condenser tube, add 10.1g (70mmol) of McBurney's acid, propanol (8mL), and toluene (80mL) respectively, heat and reflux at 110°C for 4 hours, cool to room temperature, and then add 2,4 , 5-trimethoxybenzaldehyde 9.8g (50mmol), pyridine 6.7g (85mmol), piperidine 0.75g (8.5mmol), heated to reflux for 18 hours, concentrated under reduced pressure, added ethyl acetate (20mL), water ( 30mL), extracted and separated 3 times, combined the organic phases, concentrated under reduced pressure, added ethanol (80mL), refrigerated overnight in the refrigerator, after the precipitation was precipitated, filtered with suction, washed 3 times with 50mL of ice ethanol, and obtained 7.7g of light yellow solid , yield 55%.

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Abstract

The present invention relates to α-asarol and its preparation method and application. The α-asarol involved is of structural formula I. The preparation method involves decarboxylation of 2,4,5-trimethoxybenzaldehyde and isopropylidene malonate (meldrum's acid) and fatty alcohol under the catalysis of pyridine and piperidine to obtain trans 2, 4,5-trimethoxycinnamate is then reduced with a reducing agent to obtain α-asarol. The preparation method of the invention is simple and has high yield. The application involved is the use of α-asarol in the preparation of sedative, tranquilizing, anti-Alzheimer's, anticonvulsant, anti-epileptic or cardiovascular and cerebrovascular protection drugs.

Description

technical field [0001] The invention mainly relates to a preparation method and application of α-asaroctanol, and belongs to the field of medicine synthesis and medicine technology. Background technique [0002] The International League Against Epilepsy defines epilepsy as a brain disorder characterized by the persistence of persistent changes in the brain that can produce seizures, with corresponding neurobiological, cognitive, psychological, and sociological consequences. Epilepsy patients account for 1-2% of the world's population [White H.S. Epilepsia. 2003, 44, 2]. [0003] Phenobarbital, phenytoin, and carbamazepine are first-generation antiepileptic drugs. In contrast, levetiracetam, oxcarbazepine, rufinamide, etc., as second-generation antiepileptic drugs, have the advantages of good pharmacokinetics, low toxicity, safety, and high efficiency [Prunetti P.Curr.Opin.Neurol .2011, 24, 159]. Although the second-generation antiepileptic drugs have partially improved t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/23C07C41/26A61P25/20A61P25/28A61P25/08A61P9/00
Inventor 郑晓晖白亚军秦方刚王世祥张毅刘佩何希瑞
Owner NORTHWEST UNIV
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