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Monoamine oxidase B inhibitor with potential iron chelating activity and application thereof

A hybrid, compound technology that can be used in organic chemistry, drug combinations, neurological diseases, etc., to solve problems such as poor selectivity

Pending Publication Date: 2022-03-08
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these MAOs inhibitors, which have been widely introduced into clinical practice, are limited in application due to poor selectivity and adverse reactions such as hepatotoxicity, orthostatic hypotension, and hypertensive crisis.

Method used

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  • Monoamine oxidase B inhibitor with potential iron chelating activity and application thereof
  • Monoamine oxidase B inhibitor with potential iron chelating activity and application thereof
  • Monoamine oxidase B inhibitor with potential iron chelating activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] N-(2-(2-methyl-3-hydroxy-1(4H)-4-oxopyridyl)ethyl)-4-oxo-4H-chromene-3-carboxamide (a1) preparation method

[0046] Add 2-hydroxyacetophenone (1.36g, 10mmol) and anhydrous N,N-dimethylformamide (20mL) into a 100mL single-necked bottle, stir at -15°C for 1h, and then pass through a constant pressure dropping funnel Phosphorus oxychloride (3.825g, 25mmol) was slowly added dropwise to the reaction solution, and after the dropwise addition was completed, it was transferred to room temperature and continued to stir for 14 hours. After washing with diethyl ether, a light yellow solid (1.55 g) was obtained with a yield of 89%.

[0047] Add the above light yellow solid (0.522g, 3mmol) into a 250mL single-necked bottle, dissolve it in 50ml of dichloromethane, then dissolve sulfamic acid (1.748g, 18mmol) in water (40mL) and add, stir at -2°C After 0.5h, slowly add an aqueous solution (25mL) of sodium chlorite (1.628g, 18mmol) dropwise to the reaction solution through a constant...

Embodiment 2

[0052] N-(2-(2-methyl-3-hydroxy-1(4H)-4-oxopyridyl)ethyl)-4-oxo-6-methyl-4H-benzopyran-3- The preparation method of formamide (a2)

[0053] Add 2-hydroxy-5-methylacetophenone (1.50g, 10mmol) and anhydrous N,N-dimethylformamide (20mL) into a 100mL single-necked bottle, stir at -15°C for 1h, and pass Slowly drop phosphorus oxychloride (3.825g, 25mmol) into the reaction solution with a constant pressure dropping funnel, transfer to room temperature after the dropwise addition and continue to stir for 14h. After the reaction, pour into ice water to precipitate solids, filter, After washing with water and then with ether, a light yellow solid (1.64 g) was obtained with a yield of 87.2%.

[0054] Add the above light yellow solid (0.564g, 3mmol) into a 250mL single-necked bottle, dissolve it in 51ml of dichloromethane, then dissolve sulfamic acid (1.748g, 18mmol) in water (42mL) and add, stir at -2°C After 0.5h, slowly add an aqueous solution (25mL) of sodium chlorite (1.628g, 18mm...

Embodiment 3

[0059] N-(2-(2-methyl-3-hydroxy-1(4H)-4-oxopyridyl)ethyl)-4-oxo-7-methyl-4H-benzopyran-3- The preparation method of formamide (a3)

[0060] Add 2-hydroxy-4-methylacetophenone (1.50g, 10mmol) and anhydrous N,N-dimethylformamide (20mL) into a 100mL single-necked bottle, stir at -15°C for 1h, and pass Slowly drop phosphorus oxychloride (3.825g, 25mmol) into the reaction solution with a constant pressure dropping funnel, transfer to room temperature after the dropwise addition and continue to stir for 14h. After the reaction, pour into ice water to precipitate solids, filter, Washed with water and then with diethyl ether to obtain a light yellow solid (1.59 g), yield 84.6%.

[0061] Add the above light yellow solid (0.564g, 3mmol) into a 250mL single-necked bottle, dissolve it in 51ml of dichloromethane, then dissolve sulfamic acid (1.748g, 18mmol) in water (42mL) and add, stir at -2°C After 0.5h, slowly add an aqueous solution (25mL) of sodium chlorite (1.628g, 18mmol) dropwise...

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Abstract

According to the invention, a monoamine oxidase inhibitor with iron ion chelating activity is synthesized, and a pyridone derivative with iron ion chelating activity and a chromone mother nucleus with MAO-B inhibitory activity are innovatively and organically combined together; the compound has remarkable advantages on neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease with complex pathogenesis.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of monoamine oxidase B inhibitors with iron ion chelating activity and a preparation method thereof, as well as its use in the preparation and treatment of depression and neurodegenerative syndromes (such as Parkinson's and Alzheimer's). Use in medicines for diseases such as Haimer's disease). Background technique [0002] Monoamine oxidases (MAO, EC 1.4.3.4) are a class of enzymes containing the covalently bound redox cofactor flavin adenine dinucleotide (FAD). This enzyme widely exists in the mitochondrial outer membrane tissue of mammals and is distributed in different cells of the central and peripheral nervous systems. The enzyme's role includes catalyzing the oxidative deamination of endogenous and exogenous amines to generate corresponding aldehydes. In humans, it exists mainly in two isoforms: MAO-A and MAO-B. This classification is base...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12A61P25/16A61P25/28
CPCC07D405/12A61P25/16A61P25/28
Inventor 谢媛媛张雨佳郭嘉楠张婧祺吕杨静
Owner ZHEJIANG UNIV OF TECH
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