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Formamide pyridone iron chelating agent derivative with potential multi-target anti-AD activity as well as preparation method and application thereof

A technology of carboxamide pyridone and iron chelating agent, which is applied in the direction of anti-toxins, drug combinations, nervous system diseases, etc., and can solve the problems of difficult research and development of anti-AD drugs and complicated pathogenesis

Active Publication Date: 2020-11-27
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the pathogenesis of AD is very complex. Mechanisms such as neurocholine transmitters, amyloid, Tau protein, metal ions, oxidative stress, and inflammation are interrelated and interact, which together lead to and promote the occurrence and development of AD. Therefore, The development of anti-AD drugs is also very arduous

Method used

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  • Formamide pyridone iron chelating agent derivative with potential multi-target anti-AD activity as well as preparation method and application thereof
  • Formamide pyridone iron chelating agent derivative with potential multi-target anti-AD activity as well as preparation method and application thereof
  • Formamide pyridone iron chelating agent derivative with potential multi-target anti-AD activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Example 1 The preparation method of N-(2-(2-methyl-3-hydroxyl-1(4H)-4-oxopyridyl)ethyl)-benzamide (11a)

[0069]

[0070] Add maltol (7.56g, 60mmol), p-methoxybenzyl chloride (28.19g, 180mmol), anhydrous potassium carbonate (24.84g, 180mmol), acetone (100mL) into a 250mL single-necked bottle, heat to reflux for 12 hours, TLC Monitor the reaction, stop the reaction after the conversion of the raw materials is complete, concentrate the reaction solution to obtain a solid, add water (100mL) to dissolve, extract with dichloromethane (100mL×4), combine the organic layers, dry the organic layer with anhydrous sodium sulfate, and concentrate 2-Methyl-3-p-methoxybenzyloxypyran-4-one (14.61 g) was obtained as a yellow oily liquid with a yield of 99%.

[0071] Pyrone (4.92g, 20mmol), ethylenediamine (1.26g, 21mmol), sodium hydroxide (0.72g, 18mmol), ethanol (20mL), water (18mL), and Heat at reflux at 70°C for 1.5h. After the reaction, concentrate the reaction solution and pur...

Embodiment 2

[0075] Example 2 The preparation method of N-(2-(2-methyl-3-hydroxyl-1(4H)-4-oxopyridyl)ethyl)-2-methoxybenzamide (11b)

[0076]

[0077] Add maltol (7.56g, 60mmol), p-methoxybenzyl chloride (28.19g, 180mmol), anhydrous potassium carbonate (24.84g, 180mmol), acetone (100mL) into a 250mL single-necked bottle, heat to reflux for 12 hours, TLC Monitor the reaction, stop the reaction after the conversion of the raw materials is complete, concentrate the reaction solution to obtain a solid, add water (100mL) to dissolve, extract with dichloromethane (100mL×4), combine the organic layers, dry the organic layer with anhydrous sodium sulfate, and concentrate 2-Methyl-3-p-methoxybenzyloxypyran-4-one (14.61 g) was obtained as a yellow oily liquid with a yield of 99%.

[0078] Pyrone (4.92g, 20mmol), ethylenediamine (1.26g, 21mmol), sodium hydroxide (0.72g, 18mmol), ethanol (20mL), water (18mL), and Heat at reflux at 70°C for 1.5h. After the reaction, concentrate the reaction solutio...

Embodiment 3

[0082] Example 3 The preparation method of N-(2-(2-methyl-3-hydroxyl-1(4H)-4-oxopyridyl)ethyl)-3-methoxybenzamide (11c)

[0083]

[0084] Add maltol (7.56g, 60mmol), p-methoxybenzyl chloride (28.19g, 180mmol), anhydrous potassium carbonate (24.84g, 180mmol), acetone (100mL) into a 250mL single-necked bottle, heat to reflux for 12 hours, TLC Monitor the reaction, stop the reaction after the conversion of the raw materials is complete, concentrate the reaction solution to obtain a solid, add water (100mL) to dissolve, extract with dichloromethane (100mL×4), combine the organic layers, dry the organic layer with anhydrous sodium sulfate, and concentrate 2-Methyl-3-p-methoxybenzyloxypyran-4-one (14.61 g) was obtained as a yellow oily liquid with a yield of 99%.

[0085] Pyrone (4.92g, 20mmol), ethylenediamine (1.26g, 21mmol), sodium hydroxide (0.72g, 18mmol), ethanol (20mL), water (18mL), and Heat at reflux at 70°C for 1.5h. After the reaction, concentrate the reaction solutio...

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Abstract

The invention provides a formamide pyridone iron chelating agent derivative shown as a formula (I) or a formula (II) which is described in the specification and a preparation method and application thereof. The formamide pyridone iron chelating agent derivative shown in the formula (I) or the formula (II) and the pharmaceutically acceptable salt thereof have the effects of inhibiting monoamine oxidase, chelating metal iron ions, resisting A beta and resisting oxidation activity. The derivative can be used for preparing medicines for resisting Alzheimer's disease, Parkinson's disease or other diseases treated by inhibiting monoamine oxidase, chelating metal iron ions, resisting A beta and resisting oxidation.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of carboxamide pyridones that have both iron ion chelating ability and monoamine oxidase B inhibitory effect, and synergistically realize anti-Aβ and anti-oxidation multi-target anti-Alzheimer's disease An iron-like chelator derivative, a preparation method thereof, and an application in the preparation of a drug for treating Alzheimer's disease. Background technique [0002] At present, with the incidence and number of Alzheimer's disease (AD) increasing year by year, AD has become the third deadly disease in the world after cardiovascular disease and tumor, and has seriously threatened human beings. The health of AD patients has also brought a huge burden to the family and society, and the research and development of anti-AD drugs is imminent. However, the pathogenesis of AD is very complex. Mechanisms such as neurocholine transmitters, amyloid...

Claims

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Application Information

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IPC IPC(8): C07D213/69A61P25/16A61P25/28A61P39/06
CPCC07D213/69A61P25/16A61P25/28A61P39/06Y02P20/55
Inventor 谢媛媛蒋筱莹郭嘉楠张雨佳
Owner ZHEJIANG UNIV OF TECH
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