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Tacrine-coumarin derivative containing triazole and application of derivative

A technology of coumarin derivatives and triazole bases, applied in the field of biomedicine, can solve the problems of low bioavailability, high liver toxicity and the like

Active Publication Date: 2016-04-20
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned inhibitors have defects in varying degrees. Because they only target a single cause, they cannot reverse or cure the disease, and they also have problems such as high liver toxicity and low bioavailability. Therefore, new multi-target drugs have been developed for the treatment of Alzheimer's disease. very necessary and urgent
[0006] Chinese patent "Preparation method of anti-Alzheimer's disease drug Lu-AE-58054", application number 201410420968.X discloses a new method for preparing Lu-AE-58054, the raw material is cheap, the yield is high, and it is suitable for industrial production , but there is still a problem of liver toxicity

Method used

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  • Tacrine-coumarin derivative containing triazole and application of derivative
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  • Tacrine-coumarin derivative containing triazole and application of derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0065] Synthesis of 2-(7-(2-carbonyl-4-methyl-2H-chromene)methoxy)propargyl acetate

[0066] Dissolve propargyl alcohol (10mmol) in dry dichloromethane (20mL), add triethylamine (11mmol), cool in an ice bath to 0°C, add chloroacetyl chloride (11mmol) dropwise, the reaction solution gradually turns brown, and the dropwise After that, the temperature was raised naturally for 2 hours, the reaction was stopped, washed with water, extracted with dichloromethane, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a reddish-brown liquid, which was dissolved in acetone / tetrahydrofuran and mixed Solvent (15mL, v:v=1:1), add 7-hydroxycoumarin (7mmol), potassium carbonate (7mmol), heat to 60°C for about 12h, stop the reaction, wash with water, extract with dichloromethane, organic After the phases were combined, they were washed once with saturated brine, dried over anhydrous sodium sulfate, filtere...

Embodiment 2

[0069] Synthesis of 2-(7-(2-carbonyl-4-methyl-2H-chromene)methoxy)propargyl acetate

[0070] Dissolve propargyl alcohol (10mmol) in dry dichloromethane (20mL), add triethylamine (11mmol), cool in an ice bath to 0°C, add chloroacetyl chloride (11mmol) dropwise, the reaction solution gradually turns brown, and the dropwise After that, the temperature was raised naturally for 2 hours, the reaction was stopped, washed with water, extracted with dichloromethane, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a reddish-brown liquid, which was dissolved in acetone / tetrahydrofuran and mixed Solvent (15mL, v:v=1:1), add 4-methyl-7-hydroxycoumarin (7mmol), potassium carbonate (7mmol), heat to 60°C for about 12h, stop the reaction, add water to wash, two Extracted with methyl chloride, combined the organic phases and washed once with saturated brine, dried over anhydrous sodium sulfate, filtered...

Embodiment 3

[0073] Synthesis of 2-(7-(2-carbonyl-4-phenyl-2H-chromene)methoxy)propargyl acetate

[0074] Dissolve propargyl alcohol (10mmol) in dry dichloromethane (20mL), add triethylamine (11mmol), cool in an ice bath to 0°C, add chloroacetyl chloride (11mmol) dropwise, the reaction solution gradually turns brown, and the dropwise After that, the temperature was raised naturally for 2 hours, the reaction was stopped, washed with water, extracted with dichloromethane, the organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain a reddish-brown liquid, which was dissolved in acetone / tetrahydrofuran and mixed Solvent (15mL, v:v=1:1), add 4-phenyl-7-hydroxycoumarin (7mmol), potassium carbonate (7mmol), heat to 60°C for about 12h, stop the reaction, add water to wash, two After extraction with methyl chloride, the organic phases were combined and washed once with saturated brine, dried over anhydrous sodium sulfa...

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Abstract

The invention relates to a tacrine-coumarin derivative containing triazole and an application of the derivative and belongs to the technical field of biological medicine. The derivative comprises compounds represented as a formula I and pharmaceutically acceptable salt, and three preparation methods of the derivative are provided; a pharmacological experiment proves that the derivative is acetylcholinesterase inhibitor and can inhibit activity of acetylcholin esterase, butyrylcholine esterase and MAO (monoamine oxidase), and meanwhile, the derivative can inhibit autopolymerization of beta-amyloid protein, delay hydrolysis of acetyl choline and autopolymerization of beta-amyloid protein, improve the function of acetyl choline on synapsis and be used for treating Alzheimer's disease effectively.

Description

technical field [0001] The invention relates to a tacrine-coumarin derivative containing a triazole group and its application, in particular to a tacrine-coumarin derivative containing a triazole group and its anti-Alzheimer The application in mutism drugs belongs to the technical field of biomedicine. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease with insidious onset and progressive development. Clinically, it is characterized by comprehensive dementia such as memory impairment, aphasia, apraxia, agnosia, visual-spatial skill impairment, executive dysfunction, and personality and behavior changes. Those who develop before the age of 65 are called Alzheimer's dementia; those who develop after the age of 65 It is called senile dementia, which is a disease caused by many factors. The exact cause is still not conclusively clarified. Family history, female, head trauma, low education level, thyroid disease, maternal age too high or too lo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14A61P25/28
CPCC07D405/14
Inventor 董长治王刚黄江王荣全霖阳
Owner GUANGDONG UNIV OF TECH
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