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4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compounds and their preparation methods and uses

A tetrahydroisoquinoline, carbamate technology, applied in the directions of drug combination, organic chemistry, pharmaceutical formulations, etc., can solve the problems of poor therapeutic effect and poor inhibitory activity, and achieve the improvement of motor function and reaction ability, inhibition of Significant, dose-dependent improvement in activity

Inactive Publication Date: 2020-07-14
NANYANG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In previous reports, scutellarin aglycon carbamate derivatives (CN10337956A, CN102603698A), stilbene or ethane carbamate compounds (CN102816090A), and isoflavone carbamate compounds (CN102827131A) were discovered. Although ferulic acid carbamate compounds (CN105837497A, CA105601540A, CN105646289A) these compounds have better acetylcholinesterase inhibitory activity and antioxidant activity, and Aβ aggregation has a little inhibitory effect, simultaneously to butyrylcholinesterase The inhibitory activity of these compounds is very poor, resulting in the suboptimal efficacy of these compounds in the treatment of AD in animal models

Method used

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  • 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compounds and their preparation methods and uses
  • 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compounds and their preparation methods and uses
  • 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compounds and their preparation methods and uses

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Embodiment 1

[0046] A kind of 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compound, its general chemical structure formula is:

[0047]

[0048] Wherein, in embodiment 1-49, X, R and R 1 NR 2 The substituents are detailed in Table 1.

[0049] The preparation method of the 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compound (I-1) of the above-mentioned embodiment 1 comprises the following steps:

[0050] a. Add 10mmol ferulic acid, 30mL dry THF, 15mmol EDCI, 15mmol HOBT, 10mmol substituted 1,2,3,4-tetrahydroisoquinoline into the reaction flask, stir and react at 25°C for 24h; after the reaction, depressurize Evaporate the solvent, add 50mL of dichloromethane to the residue, wash with saturated aqueous sodium carbonate solution and saturated aqueous sodium chloride solution successively, filter the organic layer after drying over anhydrous sodium sulfate, evaporate the solvent under reduced pressure, and the residue is subjected to column chromatography Purify (dic...

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Abstract

The invention discloses a 4-carbamate-feruloylagmatine-1,2,3,4-tetrahydroisoquinoline compound, and a preparation method and the application of the compound. The preparation method comprises the stepsof taking ferulic acid as a starting material to react with substituted 1,2,3,4-tetrahydroisoquinoline under the action of a first solvent and a condensing agent to form a corresponding feruloylagmatine compound, and allowing the feruloylagmatine compound and carbamyl chloride to give an acylation reaction under the action of a second solvent and an alkaline condition to form the 4-carbamate-feruloylagmatine-1,2,3,4-tetrahydroisoquinoline compound. The 4-carbamate-feruloylagmatine-1,2,3,4-tetrahydroisoquinoline compound is novel in chemical structure; chemical reactions in a preparation process are thorough; a product yield is high; the operation is convenient; and the compound is low in cost and can be extensively used for prevention and treatment of neurodegenerative diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and specifically relates to a 4-carbamate-ferulamide-1,2,3,4-tetrahydroisoquinoline compound, a preparation method and application thereof. Background technique [0002] Alzheimer's disease (AD) is one of the diseases with the highest morbidity and mortality among the elderly. According to the "2015 Global Alzheimer's Report" released by Alzheimer's Disease International (ADI), more than 46 million people in the world suffered from dementia in 2015. It is predicted that by 2050, the world's There will be 131.5 million people suffering from dementia, and the incidence rate of dementia patients in China has reached 6.61%. With the prolongation of the average life expectancy, the disease has developed into a major burden on the society and the medical care system, and has brought heavy mental and economic pressure to the society, patients and their families. Therefore, it is of great significanc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/08C07D401/12A61K31/472A61K31/4725A61K31/496A61P25/28
CPCA61P25/28C07D215/08C07D401/12
Inventor 桑志培王柯人柳文敏时健程新峰于林涛冉亚文
Owner NANYANG NORMAL UNIV