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3-hydroxy chalcone Mannich base compound and preparation and application methods thereof

A technology of hydroxychalcone Mannich base and hydroxybenzaldehyde Mannich base, which is applied in organic chemistry, drug combination, pharmaceutical formulation, etc., can solve the problem of single action target, many toxic and side effects, and insufficient long-term curative effect of AD patients. Good and other questions

Active Publication Date: 2019-05-10
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 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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  • 3-hydroxy chalcone Mannich base compound and preparation and application methods thereof
  • 3-hydroxy chalcone Mannich base compound and preparation and application methods thereof
  • 3-hydroxy chalcone Mannich base compound and preparation and application methods thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0036] Embodiment 1 General method for the preparation of 3-hydroxychalcone Mannich base compound (I)

[0037] Add 2.0 mmol of the corresponding acetophenone compound (1), 3.0 mmol of the corresponding 3-hydroxybenzaldehyde Mannich base compound (2) and 30 ml of ethanol into the reaction flask, stir well, then add 30% KOH dropwise Aqueous solution of 12.0 mmol, stirred at room temperature for 3.0 to 40.0 hours (reaction progress tracked by TLC); after the reaction, cooled to room temperature, adjusted the pH of the reaction solution to strong acidity with 10% hydrochloric acid aqueous solution, and then adjusted the reaction solution with saturated sodium bicarbonate aqueous solution pH to weakly alkaline, evaporate ethanol under reduced pressure, add 80 mL deionized water to the residual liquid, extract three times with 240 mL dichloromethane, combine organic layers, wash with saturated aqueous sodium chloride solution, and dry over anhydrous sodium sulfate After filtration, ...

Embodiment 2

[0064] Example 2 General method for the preparation of 3-hydroxychalcone Mannich base compound (I) and acid salt formation

[0065] Add 2.0 mmol of the 3-hydroxychalcone Mannich base compound (I) obtained in the above Example 1 and 50 ml of acetone into the reaction flask, stir evenly, add 8.0 mmol of the corresponding acid, and heat up to reflux and stir for 20 minutes , cooled to room temperature after the reaction, and evaporated the solvent under reduced pressure to obtain the salt of 3-hydroxychalcone Mannich base compound (I). 1 Confirmed by H NMR and ESI-MS.

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Abstract

The invention discloses a 3-hydroxy chalcone Mannich base compound (I), medically acceptable salts of the 3-hydroxy chalcone Mannich base compound, a preparation method of the 3-hydroxy chalcone Mannich base compound, a drug combination of the 3-hydroxy chalcone Mannich base compound and application of the 3-hydroxy chalcone Mannich base compound to preparing drugs for treating and / or preventing nervous system-related diseases including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related (human immunodeficiency virus-related) disease, multiple sclerosis , amyotrophic lateral sclerosis, neuropathic pain, glaucoma, cerebral arterial thrombosis and nerve injuries caused by cerebral trauma.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to a new type of 3-hydroxychalcone Mannich base compound (I) and its pharmaceutically acceptable salt, its preparation method, pharmaceutical composition and preparation of therapeutic and / or Use in drugs for the prevention of nervous system-related diseases, including but not limited to vascular dementia, Alzheimer's disease, Parkinson's disease, Huntington's disease, HIV-related dementia, multiple sclerosis, amyotrophic lateral sclerosis , neuropathic pain, glaucoma, ischemic stroke, hemorrhagic stroke, and neurological damage caused by traumatic brain injury. Background technique [0002] Neurodegenerative diseases refer to the general term for diseases caused by chronic progressive degeneration of central nervous tissue, including Alzheimer's disease (Alzheimer's disease, AD), Parkinson's disease (Parkinson's disease, PD), Huntington's disease (Huntington disease, HD), amyotrop...

Claims

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Application Information

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IPC IPC(8): C07C225/16C07D295/112A61K31/137A61K31/4453A61P25/28A61P25/16A61P25/14A61P31/18A61P29/00A61P27/06A61P9/10
Inventor 邓勇宋青曹忠诚李玉兴
Owner SICHUAN UNIV
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