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Derivative of coumarin parallel 3-hydroxypyridine-4-ketone and preparation method and application thereof

A hydroxypyridine and coumarin technology, which is applied in the field of coumarin and hydroxypyridone compounds for the treatment of Alzheimer's disease, can solve problems such as incomplete cure of the disease

Active Publication Date: 2019-05-17
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Moreover, these five drugs can only inhibit the progression of the disease, and do not completely cure the disease.

Method used

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  • Derivative of coumarin parallel 3-hydroxypyridine-4-ketone and preparation method and application thereof
  • Derivative of coumarin parallel 3-hydroxypyridine-4-ketone and preparation method and application thereof
  • Derivative of coumarin parallel 3-hydroxypyridine-4-ketone and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0066] 3-hydroxy-1-(2-(((7-hydroxy-2-oxo-2H-benzopyran-4-yl)methyl)amino)ethyl)-2-methylpyridine-4(1H )-Ketone (Ia)

[0067] Add (3.303g, 30mmol) and 30mL of concentrated sulfuric acid to a 100mL single-necked flask, place it at -5°C and stir until it is completely dissolved, slowly add dropwise (6.600g, 40mmol) to control the reaction temperature and stir for 24h. The reaction system was poured into 300 mL ice water and stirred for 2 h, filtered and dried to obtain a white solid. The yield was 83%.

[0068] Add maltol (1.260g, 10mmol), potassium carbonate (2.740g, 20mmol), benzyl bromide (2.052g, 12mmol), 130mL acetone, and react at 56℃ for 2h in a 250mL single-necked flask, spin dry, add 100mL water to dissolve it, 80 mL of dichloromethane was extracted four times and the organic phase was combined by spin-drying to obtain a yellow oily liquid. The yield was 97%.

[0069] Take the product obtained in the second step (1.080g, 5mmol) in a 100mL single-necked flask, add 30mL ethan...

example 2

[0075] 3-hydroxy-1-(2-(((7-methoxy-2-oxo-2H-benzopyran-4-yl)methyl)amino)ethyl)-2-methylpyridine-4 (1H)-ketone (Ib)

[0076] Add (3.660g, 30mmol) and 30mL of concentrated sulfuric acid to a 100mL single-necked flask, place it at -5°C and stir until it is fully dissolved, and slowly add dropwise (6.600g, 40mmol) to control the reaction temperature and stir for 24h. The reaction system was poured into 300 mL ice water and stirred for 2 h, filtered and dried to obtain a white solid. The yield is 60%.

[0077] Add maltol (1.260g, 10mmol), potassium carbonate (2.740g, 20mmol), benzyl bromide (2.052g, 12mmol), 130mL acetone, and react at 56℃ for 2h in a 250mL single-necked flask, spin dry, add 100mL water to dissolve it, 80 mL of dichloromethane was extracted four times and the organic phase was combined by spin-drying to obtain a yellow oily liquid. The yield was 97%.

[0078] Take the product obtained in the second step (1.080g, 5mmol) in a 100mL single-necked flask, add 30mL ethanol...

example 3

[0084] 3-hydroxy-1-(2-(((7-ethoxy=yl-2-oxo-2H-benzopyran-4-yl)methyl)amino)ethyl)-2-methylpyridine -4(1H)-ketone (Ic)

[0085] Add (3.303g, 30mmol) and 30mL of concentrated sulfuric acid to a 100mL single-necked flask, place it at -5°C and stir until it is completely dissolved, slowly add dropwise (6.600g, 40mmol) to control the reaction temperature and stir for 24h. The reaction system was poured into 300 mL ice water and stirred for 2 h, filtered and dried to obtain a white solid. The yield was 83%.

[0086] Add the white solid (1.050g, 5mmol) obtained in the first step to 100mL, bromoethane (0.654g, 6mmol), potassium carbonate (0.959g, 7mmol), 40mL acetone, reflux for 4h, spin dry, add 40mL water, It was extracted 3 times with 40 mL of dichloromethane, combined and spin-dried to obtain a white yellow solid. The yield was 90%.

[0087] Add maltol (1.260g, 10mmol), potassium carbonate (2.740g, 20mmol), benzyl bromide (2.052g, 12mmol), 130mL acetone, and react at 56℃ for 2h in a ...

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Abstract

The invention provides a derivative of coumarin parallel 3-hydroxypyridine-4-ketone, pharmaceutically acceptable salts of the derivative and or pharmaceutically acceptable carriers of the derivative in the preparation of drugs for treating Alzheimer's disease and Parkinson's disease or through single inhibition of monoamine oxidase activity, ability to chelate metal iron ions or through simultaneous inhibition of monoamine oxidase activity and ability to chelate the metal iron ions.

Description

Technical field [0001] The present invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of coumarin hydroxypyridone compounds with both monoamine oxidase B inhibitory effect and iron ion chelating ability. This compound can be used as a dual-target drug to treat diseases such as Alzheimer's disease. The present invention also relates to the preparation method of these compounds and their use in the treatment of Alzheimer's disease. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease. The clinical manifestations are memory loss, cognitive dysfunction, etc., which eventually lead to patients unable to take care of themselves, which is very important for the quality of life and life safety of the elderly. Big threat. The burden on patients' physical, mental and social care is very heavy. Since the population base was large ten years ago, the number of AD patients in my country exceeded 5 million. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D405/14A61P25/28A61P25/16A61P43/00
Inventor 谢媛媛米治胜张长俊白仁仁蒋筱莹郭嘉楠
Owner ZHEJIANG UNIV OF TECH
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