A class of acetophenone oxime ester imidazole derivatives and 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: 2022-07-22
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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  • A class of acetophenone oxime ester imidazole derivatives and preparation method and application thereof
  • A class of acetophenone oxime ester imidazole derivatives and preparation method and application thereof
  • A class of acetophenone oxime ester imidazole derivatives and 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] 6.0 g, 45 mmol of aluminum chloride was added to 20 mL of 1,2-dichloroethane, and after stirring at 5 °C for 30 min, 4.0 g, 36.2 mmol of catechol (compound 1) was slowly added under stirring conditions. , and continue to stir for 20 min, then add 4.4 g, 38.6 mmol of chloroacetyl chloride at 5 °C, and naturally warm to room temperature, and then stir at room temperature for 20 h. After the reaction is completed, add 70 mL, 0.5 mol / 1 L of dilute hydrochloric acid solution was quenched, the reaction was stopped at the required stage, then the temperature was naturally raised to room temperature, stirred for 3 h, filtered to obtain a solid and washed with water;

[0036] Decolorize the wet solids, specifically: dissolving the wet solids in an ...

Embodiment 2

[0053] The preparation steps are the same as those in Example 1, except that the carboxylic acid compound is replace with Compound 6b was obtained as colorless oil, yield 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 )δ163.26,159.51,150.54,148.37,144.75,137.40,130.05,129.72,129.56,125.55,125.05,121.81,119.38,119.11,108.37,107.30,42.22,25.87 22 H 21 N 3 O 4 392.1604[M+H] + , found 392.1601.

Embodiment 3

[0055] The preparation steps are the same as those in Example 1, except that the carboxylic acid compound is replace with Compound 6c was obtained as colorless oil, yield 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 = 3.0 Hz), 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 a class of acetophenone oxime ester imidazole derivatives and a preparation method and application thereof. The invention designs and synthesizes a series of new (E)-1-(2 ,2-dimethylbenzo[d][1,3]dioxol-5-yl)-2-(1H-imidazol-1-yl)-1-ethan ketoxime ester imidazole derivatives, and further explore The inhibitory activity of these derivatives on LPS-induced neuroinflammation was investigated, and the effect of different substituents on the inhibitory activity was combined to explore the relationship between the molecular structure of the compounds and the inhibitory activity. In-depth research on inflammation, as well as the development of new Alzheimer's drugs provide experimental and theoretical basis.

Description

technical field [0001] The invention relates to the technical field of acetophenone oxime ester imidazole derivatives, in particular to a class of acetophenone oxime ester 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 imidazole ring systems play 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 (Oxiconazole) and Miconazole (Miconazole) are typical representatives of this class of compounds in terms of antibacterial, they have a wide range of inhibitory effects on fungi such as mycotoxins, and al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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