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Diaryl-containing imidazole compound and preparation method and medical application thereof

A kind of technology of diarylimidazole and compound, which is applied in the field of medicine and achieves the effect of good selectivity

Active Publication Date: 2019-02-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although no MTDL drug has entered clinical research, this new design strategy still has great potential

Method used

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  • Diaryl-containing imidazole compound and preparation method and medical application thereof
  • Diaryl-containing imidazole compound and preparation method and medical application thereof
  • Diaryl-containing imidazole compound and preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] (1) Synthesis of 2-bromo-1-(4-fluorophenyl)ethan-1-one

[0050] Take 4-fluoroacetophenone (1.38g, 10mmol), take chloroform as the reaction solvent, in Br 2 (1.91g, 12mmol), stirred at room temperature for 1h, after the reaction was completed, the reaction was quenched with saturated sodium sulfite, and the organic phase was washed with saturated sodium bicarbonate and saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to give 2.1 g of crude product.

[0051] (2) Synthesis of 1-(4-fluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

[0052] Crude 2-bromo-1-(4-fluorophenyl)ethan-1-one (2.1g, 9.67mmol) and imidazole (1.31g, 19.35mmol) were dissolved in 50ml of tetrahydrofuran, and potassium carbonate (2.67g, 19.35mmol) was added , After stirring at room temperature for 3 h, the reaction liquid was removed in vacuo, water was added, and extracted with ethyl acetate. The organic phase was washed with water and saturated brine, and drie...

Embodiment 2

[0058] (1) Synthesis of 2-bromo-1-(2,4-difluorophenyl)ethan-1-one

[0059] Take 2,4-difluoroacetophenone (1.56g, 10mmol) and dissolve it in 100ml of chloroform, slowly add Br 2 (1.91g, 12mmol), after dropping, stirred at room temperature for 1h. After the reaction was completed, the reaction was quenched with saturated sodium sulfite, and the organic phase was washed with saturated sodium bicarbonate and saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to give 2.3 g of crude product.

[0060] (2) Synthesis of 1-(2,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

[0061] Crude 2-bromo-1-(2,4-difluorophenyl)ethan-1-one (2.3g, 9.78mmol) and imidazole (1.33g, 19.57mmol) were dissolved in 50ml of tetrahydrofuran, and potassium carbonate (2.7g, 19.57 mmol), after stirring at room temperature for 3 h, the reaction solution was removed in vacuo, water was added, and extracted with ethyl acetate. The organic phase was washed with water ...

Embodiment 3

[0067] (1) Synthesis of 2-bromo-1-(3,4-difluorophenyl)ethan-1-one

[0068] Take 3,4-difluoroacetophenone (1.56g, 10mmol) and dissolve it in 100ml of chloroform, slowly add Br 2 (1.91g, 12mmol), after dropping, stirred at room temperature for 1h. After the reaction was completed, the reaction was quenched with saturated sodium sulfite, and the organic phase was washed with saturated sodium bicarbonate and saturated brine. After drying over anhydrous sodium sulfate, the solvent was removed in vacuo to give 2.3 g of crude product.

[0069] (2) Synthesis of 1-(3,4-difluorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

[0070] Crude 2-bromo-1-(3,4-difluorophenyl)ethan-1-one (2.3g, 9.78mmol) and imidazole (1.33g, 19.57mmol) were dissolved in 50ml tetrahydrofuran, and potassium carbonate (2.7g, 19.57 mmol), after stirring at room temperature for 3 h, the reaction solution was removed in vacuo, water was added, and extracted with ethyl acetate. The organic phase was washed with water and...

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Abstract

The invention discloses a diaryl-containing imidazole compound. The invention further discloses application of the diaryl-containing imidazole compound to preparation of drugs for preventing or treating Alzheimer's disease. The inventor screens butyrylcholine esterase and IDO1 as carriers for inhibiting the activity to evaluate the effect of the diaryl imidazole compound to treat Alzheimer's disease, and finds that the diaryl imidazole compound has good in vitro activity, and can be further developed as a precursor substance for performing the Alzheimer's disease resistant effect by inhibitingthe activity of cholinesterase. (The formula is shown in the description).

Description

technical field [0001] The invention belongs to the field of medicine, and relates to a diaryl imidazole compound and a preparation method thereof, and the application of the compound in the preparation of a drug for treating Alzheimer's disease. Background technique [0002] Alzheimer's disease (AD) is a neurodegenerative disease. Clinical manifestations are degenerative loss of memory and cognitive function. According to the Alzheimer's Association, AD is one of the top ten causes of death in the United States with no way to prevent, cure, or slow progression. As of 2016, there were approximately 47 million people with dementia worldwide, and this number will exceed 131 million by 2050. These numbers may still be underestimated because they do not include those in the earliest clinical stages of the disease. AD patients need long-term care. In 2015, the treatment cost of AD and other dementias in the United States reached 81.8 billion U.S. dollars, and it is expected to...

Claims

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Application Information

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IPC IPC(8): C07D233/60C07D409/06C07D405/06A61K31/4164A61K31/4178A61P25/28
CPCA61P25/28C07D233/60C07D405/06C07D409/06Y02A50/30
Inventor 孙昊鹏卢鑫李琦杨鸿瑜陈瑶李启航冯锋曲玮
Owner CHINA PHARM UNIV
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