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Flavone alkylamine compounds as well as preparation method and application thereof

A flavonoid alkylamine and compound technology, which is applied to a class of flavonoid alkylamine compounds, and the fields of their preparation and use, can solve the problems of single action target, poor long-term efficacy in AD patients, and many toxic and side effects.

Inactive Publication Date: 2013-05-08
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these drugs have problems such as single target, many toxic and side effects, and poor long-term curative effect on AD patients.

Method used

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  • Flavone alkylamine compounds as well as preparation method and application thereof
  • Flavone alkylamine compounds as well as preparation method and application thereof
  • Flavone alkylamine compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Linker said (CH 2 ) m ，R 4 and R 5 General method for the preparation of flavonoid alkylamines (I) when H is not expressed at the same time

[0062] Add 2.0 mmol of the corresponding flavonoids ( 1 ), 30 ml acetonitrile, 7.0 mmol anhydrous potassium carbonate and dibromoalkyl compound ( 2 ) 7.0 mmol, heated and refluxed and stirred for 3.0 to 12.0 hours (the reaction process was followed by TLC); after the reaction was completed, filtered while hot, a small amount of acetonitrile washed the filter cake, and the filtrate was evaporated under reduced pressure to remove the solvent and excess dibromoalkyl compounds. The product was purified by column chromatography (eluent: dichloromethane) to obtain aryloxyalkyl bromide compound ( 3 ), the yield is 45.3%-96.0%. The above-mentioned aryloxyalkyl bromide compound ( 3 ) was dissolved in 30 ml of ethanol, and 6.0 mmol of organic amine compounds ( 4), heated and refluxed and stirred for 6.0 to 16.0 hours...

Embodiment 2

[0084] Linker said (CH 2 ) m ，R 4 and R 5 General method for the preparation of flavonoid alkylamines (I) when H is represented simultaneously

[0085] Add 2.0 mmol of corresponding 6,7-hydroxyl flavonoids protected by diphenylmethylene in the reaction flask ( 5 ), 30 ml acetone, 7.0 mmol anhydrous potassium carbonate and dibromoalkyl compound ( 2 ) 7.0 mmol, heated and refluxed and stirred for 8.0 to 18.0 hours (the reaction process was tracked by TLC); after the reaction was completed, filtered while hot, a small amount of acetone washed the filter cake, and the filtrate was evaporated under reduced pressure to remove the solvent and excess dibromoalkyl compounds. The product was purified by column chromatography (eluent: dichloromethane) to obtain aryloxyalkyl bromide compound ( 6 ), the yield is 89.0%-98.6%; the above-mentioned aryloxyalkyl bromide compound ( 6 ) was dissolved in 30 ml of ethanol, and 6.0 mmol of organic amine compounds ( 4 ), heated...

Embodiment 3

[0098] Example 3 express ，R 4 and R 5 General method for the preparation of flavonoid alkylamines (I) when H is not expressed at the same time

[0099] Add 2.0 mmol of the corresponding flavonoids ( 1 ), 30 ml acetonitrile, 3.0 mmol anhydrous potassium carbonate and 2.5 mmol 1-substituted-4-chloroalkylpiperazine ( 11 ), heated and refluxed and stirred for 6.0 to 16.0 hours (the reaction process was tracked by TLC); after the reaction was completed, filtered while hot, a small amount of acetonitrile washed the filter cake, the filtrate was evaporated under reduced pressure to remove the solvent, and the residue was purified by column chromatography (eluent : Petroleum ether-ethyl acetate=30:1 v / v), to get the corresponding flavonoid alkylamines ( I ), the yield is 50.0%-82.0%, and its chemical structure has been tested 1 H-NMR, 13 Confirmed by C-NMR and ESI-MS. The structure of the target object prepared by the above-mentioned general method is as follows:

...

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Abstract

The invention discloses a type of novel flavone alkylamine compounds with the formula (I) and pharmaceutically acceptable salts, a preparation method, a pharmaceutical composition and application in preparation of medicines for treating and / or preventiung neurodegeneration related diseases. The diseases comprise but are not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV related dementia, multiple sclerosis, progressive lateral sclerosis, neuropathic pain, glaucoma and other neurodegeneration diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of flavonoid alkylamine compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation for treating and / or preventing neurodegenerative related diseases Use in medicines including, but not limited to, vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, progressive lateral sclerosis, neuropathic pain, glaucoma and other neurodegenerative diseases. Background technique [0002] Vascular dementia (VD) is a mental and cognitive disorder caused by various types of cerebrovascular diseases (including ischemic cerebrovascular disease, hemorrhagic cerebrovascular disease, acute and chronic hypoxic cerebrovascular disease, etc.). It is a clinical syndrome of cognitive dysfunction, and its main clinical manifestations include: decline in cognitive ...

Claims

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Application Information

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IPC IPC(8): C07D311/30C07D405/12C07D491/107A61K31/352A61K31/453A61K31/5377A61K31/496A61K31/473A61K31/4025A61K31/55A61P25/28A61P25/16A61P25/14A61P25/04A61P27/06
CPCC07D491/107C07D405/12A61K31/496C07D311/30A61K31/5377A61K31/352A61K31/453A61K31/473A61K31/4025A61K31/55A61P25/04A61P25/14A61P25/16A61P25/28A61P27/06
Inventor 邓勇谭正怀桑志培强晓明刘强
Owner SICHUAN UNIV
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