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Triazole alcohol compound, its preparation method and application

A compound, triazole technology, applied in organic chemistry, antifungal agents, etc., to achieve novel and effective methods, good antifungal activity in vitro, and the effect of overcoming the problem of fungal drug resistance

Inactive Publication Date: 2011-12-14
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-substituted amino)-2-propanol compounds Its simple and effective preparation method and antifungal activity report

Method used

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  • Triazole alcohol compound, its preparation method and application
  • Triazole alcohol compound, its preparation method and application
  • Triazole alcohol compound, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] (1), Preparation of 2-chloro-2',4'-difluoroacetophenone (compound 2)

[0045] Add 6.65 g (0.05 mol) of anhydrous aluminum trichloride and 9.9 ml (0.1 mol) of m-difluorobenzene into a 50 mL three-necked flask with a drying tube, then slowly add 7.7 ml (0.1 mol) of chloroacetyl chloride dropwise, at room temperature The reaction was stirred for 4 h. After the reaction was completed, a small amount of water was added under an ice bath, stirred to release heat, and then placed in a refrigerator to cool and crystallize, filtered with suction, and dried to obtain 18.6 g of a white solid (yield 98%), mp 46-48°C.

[0046] (2), prepare α-(1 H -1,2,4-Triazol-1-yl)-2,4-difluoroacetophenone (Compound 3)

[0047] Add 6.36 g (0.06 mol) of anhydrous Na to a 100 mL three-neck flask 2 CO 3 , 8.28 g ( 0.12 mol) of 1 H -1,2,4-triazole and 50 mL of dichloromethane, stirred at room temperature, then added 11.4 g (0.06 mol) of compound 2 , then slowly dropwise added 1.44 g (0.0024 mol...

Embodiment 2

[0052] Embodiment 2: preparation 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-propionyl

[0053] Amino)-2-ol (compound 6a )

[0054] In a 25 mL three-neck flask, add 0.254 g (1.0 mmol) of the prepared compound at 0°C 5 , then add 6 mL of anhydrous acetonitrile and stir to dissolve, then add 0.28ml, (2.0 mmol) triethylamine, slowly add 0.09 mL (1.0 mmol) of propionyl chloride solution in 6 mL of anhydrous acetonitrile dropwise under stirring, after the addition is complete, the mixture Turn to room temperature and stir for 2 h to stop the reaction. First filter to remove the white solid, the filtrate was evaporated to dryness under reduced pressure, the residue was dissolved in acetone, and separated by thin layer chromatography to obtain a light yellow solid 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-propionyl)-2-ol 243 mg, yield 78%, melting point 183 -184°C.

Embodiment 3

[0055] Embodiment 3: preparation 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-benzoyl

[0056] (amino)-2-ol (compound 6b)

[0057] In a 50 mL three-neck flask, add 0.51 g (2.0 mmol) of the prepared compound at 0°C 5 , then add 12 mL of anhydrous acetonitrile, stir to dissolve, then add 0.56 ml, (4.0 mmol) triethylamine, slowly add 0.24 mL (2.0 mmol) of benzoyl chloride solution in 12 mL of anhydrous acetonitrile dropwise under stirring, the addition is complete, The mixture was stirred at room temperature for 3 h to stop the reaction. First filter to remove the white solid, the filtrate was evaporated to dryness under reduced pressure, the residue was dissolved in acetone, and separated by thin layer chromatography to obtain a light yellow solid 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-propionyl)-2-ol 566 mg, yield 79%, melting point 173 -174°C.

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Abstract

The invention discloses a triazole antifungal compound and its preparation method and application, belongs to the field of pharmaceutical compounds, and specifically relates to a new triazole antifungal compound with the following general chemical structure formula. The preparation method of the compound of the present invention is economical, simple, mild and effective. The obtained compound has strong antibacterial activity against pathogenic fungi Candida albicans and Aspergillus, compared with clinical drugs fluconazole and itraconazole, it has the advantages of high efficiency and broad spectrum, and can be used to prepare new antifungal agents drug.

Description

technical field [0001] The present invention relates to the field of pharmaceutical compounds, in particular to a class of novel triazole alcohol antifungal compounds—1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorobenzene Base)-3-(N-substituted amino)-2-propanol compounds and their preparation methods and applications. Background technique [0002] Fungal infection is a common disease, which can manifest as superficial mycosis and deep mycosis. In recent years, the widespread use of broad-spectrum antibiotics has destroyed the normal flora symbiotic relationship between bacteria and fungi; the extensive use of corticosteroids, anti-tumor drugs and other immunosuppressants has also reduced the body's resistance to fungi; radiation therapy and organ Factors such as the widespread use of transplantation and the widespread availability of catheters and cannulae have contributed to the increasing incidence and severity of deep mycoses, and deep fungal infections have become a cause of...

Claims

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Application Information

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IPC IPC(8): C07D249/08C07D405/12A61K31/4196A61P31/10
Inventor 吴春丽李幸史云涛雷伟马慧艳乔家彬李爱星
Owner ZHENGZHOU UNIV
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