Homoisoflavonoid mannich base compound and preparation method and application thereof

A technology of isoflavone Mannich base and flavonoid Mannich base, which is applied in the fields of high isoflavone Mannich base compound, its preparation and use, and can solve the problem of many toxic and side effects, complex pathogenesis, single action target, etc. question

Inactive Publication Date: 2017-05-10
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] AD is a disease caused by multiple factors, and its pathogenesis is complex. Its pathogenesis has not yet been fully elucidated. However, studies have shown that the decline in the level of acetylcholine in the brain of patients, the excessive production and deposition of β-amyloid protein, and the disorder of metal ion metabolism. Ca 2+ imbalance, tau - Various factors such as neurofibrillary tangles caused by protein hyperphosphorylation, excessive activity of glutamate receptors, large amounts of reactive oxygen species (ROS) and free radicals produced by oxidative stress, and neuroinflammation play an important role in the pathogenesis of AD Role
In response to the above-mentioned pathogenic factors, researchers adopted the traditional "one drug, one target" drug design strategy, and discovered a large number of drugs with high activity and high selectivity for a certain target, such as: cholinesterase inhibitors and N -methyl- D - Aspartate receptor antagonists, etc., but these drugs have problems such as a single target, more toxic and side effects in clinical use, and poor long-term curative effect on AD patients

Method used

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  • Homoisoflavonoid mannich base compound and preparation method and application thereof
  • Homoisoflavonoid mannich base compound and preparation method and application thereof
  • Homoisoflavonoid mannich base compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 General method for the preparation of high isoflavone Mannich base compounds (I)

[0035] Add 2.0 mmol of the corresponding chromanone compound (1), 3.0 mmol of the corresponding hydroxybenzaldehyde Mannich base compound (2) and 30 ml of methanol into the reaction flask. After stirring evenly, add 30% KOH aqueous solution 12.0 mmol, heated and refluxed and stirred for 3.0 to 24.0 hours (the reaction process was tracked by TLC); after the reaction, cooled to room temperature, adjusted the pH of the reaction solution to strong acidity with 10% aqueous hydrochloric acid solution, and then adjusted the pH of the reaction solution with saturated aqueous sodium bicarbonate solution To weak alkalinity, methanol was evaporated under reduced pressure, 80 mL of deionized water was added to the residual liquid, extracted three times with 240 mL of dichloromethane, the organic layers were combined, washed with saturated aqueous sodium chloride solution, dried over anhydrou...

Embodiment 2

[0043] Example 2 General method for the preparation of high isoflavone Mannich base compound (I) and acid salt formation

[0044] Add 2.0 mmol of the high isoflavone Mannich base compound (I) obtained according to the above Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, heat up and reflux and stir for 20 minutes, and the reaction is over After cooling to room temperature, the solvent was evaporated under reduced pressure, the residue was recrystallized with acetone, and the precipitated solid was filtered to obtain the salt of the high isoflavone Mannich base compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a novel homoisoflavonoid mannich base compound (I) and pharmaceutically acceptable salts, a preparation method, a pharmaceutical composition and application thereof in preparation of medicines for treatment and / or prevention of neurodegeneration related diseases. The neurodegeneration related diseases include but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV (human immunodeficiency virus) related dementia, multiple sclerosis, progressive lateral sclerosis of spinal cord, neuropathic pain, glaucoma and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of high-isoflavone Mannich base compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation for treating and / or preventing neurodegeneration Sex-related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, progressive lateral sclerosis, neurological Pain, glaucoma and other neurodegenerative diseases. Background technique [0002] Alzheimer's disease (Alzheimer's disease, AD, senile dementia) is a degenerative disease of the central nervous system mainly characterized by progressive cognitive impairment and memory impairment. Vascular diseases and cancers are high-incidence diseases, which have risen to the fourth cause of death in developed countries such as Europe and the United States. Accordin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/22A61K31/352A61K31/4025A61K31/453A61K31/5377A61K31/496A61P25/28A61P25/04A61P27/06A61P25/16A61P25/14A61P25/00
CPCC07D311/22
Inventor 邓勇李岩强晓明郑云小竹徐锐曹忠诚宋青
Owner SICHUAN UNIV
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