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Propargyl imine compounds and use thereof in preparation of MAO inhibitor

A propargyl imine compound technology, applied in the field of new propargyl imine compounds, can solve the problems of limited application, and achieve the effect of simple equipment, simple operation process and stable properties

Inactive Publication Date: 2010-05-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its application is limited because of the high blood pressure caused by "cheese reaction"

Method used

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  • Propargyl imine compounds and use thereof in preparation of MAO inhibitor
  • Propargyl imine compounds and use thereof in preparation of MAO inhibitor
  • Propargyl imine compounds and use thereof in preparation of MAO inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of (3,5-dimethyl-2-propynyl imine)-1H-pyrrole (compound 1)

[0032] (3,5-Dimethyl-1H-pyrrole)-2-carbaldehyde 0.25g (2mmol) was dissolved in dry THF (100ml), after the dissolution was complete, 4.0ml (60mmol) of propargylamine, anhydrous magnesium sulfate 5.0 g (40mmol), stirred at room temperature for 48h. Filter the filtrate to remove the solvent with a rotary evaporator, extract the residue with dichloromethane, wash with saturated brine (100ml) and saturated sodium bicarbonate solution (100ml), separate the organic layer, dry over anhydrous magnesium sulfate, filter, and evaporate to dryness , to obtain the crude product, column chromatography (silica gel is the stationary phase, the developer is ethyl acetate / petroleum ether, gradient concentration, the product is obtained when the volume ratio of ethyl acetate / petroleum ether is 1:1, the same below), and a yellow solid 0.278 g, yield 87%.

[0033]

Embodiment 2

[0034] Embodiment 2: the synthesis of diphenylpropynyl imine (compound 2)

[0035] Dissolve 0.36g (2mmol) of benzophenone and 4ml of propargylamine in dry 15ml of dichloromethane, cool to -20°C, add 3ml of titanium tetrachloride with a syringe, and react at room temperature for 3 days. After the reaction is complete, filter , adding dichloromethane to the filtrate for extraction, washing with saturated brine and sodium bicarbonate solution, separating the organic layer, drying over anhydrous magnesium sulfate, filtering, and evaporating to dryness to obtain the crude product, which was purified by column chromatography to obtain 0.4166g of a yellow liquid, Yield 96%.

[0036]

Embodiment 3

[0037] Example 3: Synthesis of (5,6-dimethoxy)phenylpropynyl imine (compound 18)

[0038] Dissolve 0.332g (2mmol) of 5,6-dimethoxybenzaldehyde in 100ml of benzene, add 2ml of propargylamine, 0.5g of anhydrous magnesium sulfate, reflux at 80°C for 18h, filter, and remove the solvent from the filtrate with a rotary evaporator , the residue was extracted with dichloromethane, washed with saturated brine (100ml) and saturated sodium bicarbonate solution (100ml), separated the organic layer, dried over anhydrous magnesium sulfate, filtered, and evaporated to dryness to obtain crude product, column chromatography, to obtain Reddish-brown liquid 0.37g, yield 92%.

[0039]

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PUM

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Abstract

The invention provides use of propargyl imine compounds in the preparation of a monoamine oxidase inhibitor and new propargyl imine compounds. The propargyl imine compounds have a structural formula (I). The invention has the advantages that: (1) equipment required for the preparation of the propargyl imine compounds is simple, the operation process is simple and convenient, the raw material sources are commercialized and readily available and the compounds serving as the monoamine oxidase inhibitor are stable in nature and high in purity (over 99 percent); and (2) compared with the traditional monoamine oxidase inhibitor, the monoamine oxidase inhibitor prepared from the new propargyl imine compounds has a simpler structure, a higher inhibition activity, higher MAO-A selectivity and higher MAO-B selectivity.

Description

(1) Technical field [0001] The invention relates to the application of propargyl imine compounds in the preparation of monoamine oxidase (MAO) inhibitors and a new class of propargyl imine compounds. (2) Background technology [0002] Since the anti-tuberculosis drug isoniazid was found to be a potential MAO inhibitor, research on MAO inhibitors has become a hot topic. Iproniazid became the first MAO inhibitor, because it was discovered that this kind of MAO inhibitor containing hydrazine structure can also inactivate P450s and cause liver toxicity; and studied the non-hydrazine MAO inhibition represented by tranylcypromine Agents, this category can be called the second generation. But because "cheese reaction" causes high blood pressure, its application is limited. Therefore, it is quite necessary and urgent to develop a newer and more efficient monoamine oxidase inhibitor. (3) Contents of the invention [0003] The purpose of the present invention is to provide a new ...

Claims

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Application Information

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IPC IPC(8): A61K31/40A61K31/137A61K31/4402A61K31/47A61K31/341C07D207/335C07C251/24C07D213/53C07D215/18C07D307/52A61P31/06
Inventor 朱勍贾朝
Owner ZHEJIANG UNIV OF TECH
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