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Acetophenone oxime ester imidazole derivative as well as preparation method and application thereof

A technology of acetophenone oxime ester imidazole and derivatives is applied in the field of acetophenone oxime ester imidazole derivatives and preparation thereof, and can solve the problems of few activity reports, no activity reports and the like

Active Publication Date: 2021-09-24
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, the agricultural research on acetophenone imidazole oxime derivatives has become more and more in-depth, but there are relatively few reports on other activities, especially in the anti-neuritis and treatment of Alzheimer's disease.

Method used

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  • Acetophenone oxime ester imidazole derivative as well as preparation method and application thereof
  • Acetophenone oxime ester imidazole derivative as well as preparation method and application thereof
  • Acetophenone oxime ester imidazole derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Preparation of (E)-1-(2,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-(1H-imidazol-1-yl)ethanone oxime ester method, including the following steps:

[0034] (1) Preparation of 2-chloro-1-(3,4-dihydroxyphenyl)ethanone (compound 2):

[0035] Add 6.0 g, 45 mmol of aluminum chloride to 20 mL of 1,2-dichloroethane, stir at 5°C for 30 min, then slowly add 4.0 g, 36.2 mmol of catechol (compound 1) under stirring conditions , and continued to stir for 20min, then added 4.4g, 38.6mmol of chloroacetyl chloride at 5°C, and naturally warmed up to room temperature, and then stirred at room temperature for 20h. After the reaction was completed, 70mL, 0.5mol / L of dilute hydrochloric acid solution was quenched, the reaction was stopped at the desired stage, and then naturally warmed to room temperature and stirred for 3 h, the solid was obtained by filtration and washed with water;

[0036] The wet solid is decolorized, specifically: the wet solid is dissolved in acetic acid aqueous solutio...

Embodiment 2

[0053] The same as the preparation steps of Example 1, the only difference is that the carboxylic acid compound is made of replace with Compound 6b was obtained as a colorless oil with a yield of 48%; 1 H NMR (500MHz, CDCl 3 )δ7.93(d, J=8.0Hz, 2H), 7.59(s, 1H), 7.30(d, J=8.0Hz, 2H), 7.22(s, 1H), 7.17(d, J=8.0Hz, 1H), 7.06(s, 1H), 6.97(s, 1H), 6.74(d, J=8.1Hz, 1H), 5.36(s, 2H), 2.44(s, 3H), 1.69(s, 6H); 13 C NMR (125MHz, CDCl 3 )δ163.26, 159.51, 150.54, 148.37, 144.75, 137.40, 130.05, 129.72, 129.56, 125.55, 125.05, 121.81, 119.38, 119.11, 108.37, 107.30, 42.22HR215.7c 22 h 21 N 3 o 4 392.1604[M+H] + , found 392.1601.

Embodiment 3

[0055] The same as the preparation steps of Example 1, the only difference is that the carboxylic acid compound is made of replace with Compound 6c was obtained as a colorless oil with a yield of 54%; 1 H NMR (500MHz, CDCl 3 )δ8.07(dd,J=7.7Hz,5.7Hz,2H),7.61(s,1H),7.26–7.15(m,4H),7.10(s,1H),6.98(s,1H),6.78( d,J=8.1Hz,1H),5.37(s,2H),1.72(s,6H); 13 C NMR (125MHz, CDCl 3 )δ166.31(d,J C-F =255.8Hz), 162.37, 159.81, 150.80, 148.54, 137.41, 132.40 (d, J C-F =9.5Hz), 130.29, 124.95, 124.69 (d, J = 3.0Hz), 121.94, 119.59, 119.12, 116.25 (d, J C-F =22.2Hz), 108.53, 107.36, 42.42, 25.98; .HRMS(ESI) m / z: calcd for C 21 h 18 FN 3 o 4 396.1354[M+H] + , found 396.1352.

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Abstract

The invention relates to the technical field of acetophenone oxime ester imidazole derivatives, in particular to acetophenone oxime ester imidazole derivatives as well as a preparation method and application thereof. According to the invention, a series of novel (E)-1-(2, 2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-(1H-imidazole-1-yl)-1-ethanone oxime ester imidazole derivatives are designed and synthesized. The invention further explores the inhibitory activity of the derivative on LPS-induced neuroinflammation, and discusses the interrelation between the molecular structure of the compound and the inhibitory activity in combination with the influence of different substituents on the inhibitory activity, thereby further widening the deep study of the imidazole derivative on the aspect of neuritis resistance, and providing the experimental and theoretical bases for developing a novel medicine for treating the Alzheimer's disease.

Description

technical field [0001] The invention relates to the technical field of acetophenone oxime imidazole derivatives, in particular to a class of acetophenone oxime imidazole derivatives and a preparation method and application thereof. Background technique [0002] Imidazole derivatives have always been a research hotspot at home and abroad, and the imidazole ring system plays an important role in medicinal chemistry including organic synthesis. Acetophenone imidazole oxime derivatives have attracted attention due to their considerable insecticidal, antibacterial, herbicidal, and anti-plant virus activities. Oxime structures have become common groups in pesticide research and development, and most of these structures have low toxicity. Efficient advantages. Oxiconazole and miconazole are typical representatives of this type of compound in terms of antibacterial properties. They have a wide range of inhibitory effects on fungi such as mold pathogens, and also have inhibitory eff...

Claims

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Application Information

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IPC IPC(8): C07D405/06A61P25/00A61P29/00A61K31/4178
CPCC07D405/06A61P25/00A61P29/00
Inventor 汤江江任博刘荣春黄兰芳
Owner NORTHWEST A & F UNIV
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