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Triazole aromatic alcohol heterocyclic ether derivative and preparing method and application thereof

A kind of triazolam, aromatic heterocycle technology, applied in triazolam aromatic heterocyclic ether derivatives and preparation field thereof

Inactive Publication Date: 2016-01-13
王倩
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Chinese patent document CN201510106679.7 discloses a triazole alcohol derivative and its preparation method and application, and Chinese patent document CN201310034677.2 discloses a novel triazole antifungal compound, its pharmaceutical composition and its preparation method and purposes, Chinese patent document 200410016186.6 discloses a 3-substituted piperazine triazole antifungal compound and its salts, but so far there is no relevant triazole aromatic heterocyclic ether compound and its antifungal active report

Method used

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  • Triazole aromatic alcohol heterocyclic ether derivative and preparing method and application thereof
  • Triazole aromatic alcohol heterocyclic ether derivative and preparing method and application thereof
  • Triazole aromatic alcohol heterocyclic ether derivative and preparing method and application thereof

Examples

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Embodiment 1

[0150] Example 1: 1-(5-(4-cyanophenyl)pyridyl-2-oxyl)-2-(2,4-difluorophenyl)-3-(1H-1,2,4- Synthesis of triazol-1-yl)propyl-2-ol

[0151] Step 1: Dissolve 4-cyanophenylboronic acid (5mmol), 2-fluoro-5-bromopyridine (5mmol), potassium carbonate (10mmol) and tetrakistriphenylphosphine palladium (5mol%) in toluene (20mL), Add water (2mL), react at 100°C for 5 hours, extract with ethyl acetate after the reaction is complete, wash the organic phase three times with saturated aqueous sodium chloride solution, dry over anhydrous sodium sulfate and spin to dry column chromatography to obtain 4-(6 -fluoropyridin-3-yl)benzonitrile (820 mg).

[0152] Step 2: Add 1-((2-(2,4-difluorophenyl)oxiran-2-yl)methyl)-1H-1,2,4-triazolemethanesulfonate (50mmol) Dissolve in water, add concentrated sulfuric acid (10mL), react at room temperature for 2 hours, neutralize with sodium bicarbonate and extract with ethyl acetate, wash the organic phase with saturated aqueous sodium chloride, dry with anhyd...

Embodiment 2

[0154] Example 2: 1-(5-(4-cyanophenyl)-3-fluoropyridyl-2-oxyl)-2-(2,4-difluorophenyl)-3-(1H-1, Synthesis of 2,4-triazol-1-yl)propyl-2-ol

[0155] 4-(5,6-difluoropyridin-3-yl)benzonitrile (1mmol), 2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole -1-yl)propane-1,2-diol (1mmol) was dissolved in dimethyl sulfoxide, cesium carbonate (2mmol) was added, and reacted at 50°C for 16 hours. After the reaction was complete, the solid was filtered off, and the filtrate was spin-dried Post-column chromatography prepared the target product (110 mg).

Embodiment 3

[0156] Example 3: 1-(5-(4-difluoromethoxyphenyl)pyridyl-2-oxyl)-2-(2,4-difluorophenyl)-3-(1H-1,2 , Synthesis of 4-triazol-1-yl)propyl-2-ol

[0157] 2-fluoro-5-(4-difluoromethoxyphenyl)pyridine (1mmol), 2-(2,4-difluorophenyl)-3-(1H-1,2,4-triazole -1-yl)propane-1,2-diol (1mmol) was dissolved in dimethyl sulfoxide, cesium carbonate (2mmol) was added, and reacted at 50°C for 16 hours. After the reaction was complete, the solid was filtered off, and the filtrate was spin-dried Post-column chromatography prepared the target product (100 mg).

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Abstract

The invention relates to a triazole aromatic alcohol heterocyclic ether derivative and the preparing method and application thereof, and particularly provides the general structure, crystal form, pharmaceutically acceptable inorganic acid salt or organic acid salt, aquo-complex, and solvate or prodrug of the triazole aromatic alcohol heterocyclic ether derivative. In-vitro and in-vivo bacteriostasis experiments prove that the compound has remarkable activity in inhibiting human body pathomycete candida albicans, candida parapsilosis, cryptococcus neoformans, candida glabrata, aspergillus fumigates, gypseous microsporum and trichophyton rubrum, and the activity is higher than that of fluconazole. Furthermore, the compound has the advantages of being low in toxicity, wide in antifungal spectrum and the like, and therefore the compound can be used for preparing antifungal drugs.

Description

technical field [0001] The invention relates to the technical field of medical compounds, in particular to a triazole aromatic heterocyclic ether derivative and its preparation method and application. Background technique [0002] With the continuous increase in the incidence of tumors, the widespread implementation of bone marrow and organ transplantation, and the substantial increase in the use of immunosuppressants and broad-spectrum antibiotics, deep fungal infections have become more and more common clinical problems. Systemic deep fungal infection seriously endangers the life of patients, and the mortality rate is as high as 50%. In particular, anti-deep fungal drugs are very scarce, far from meeting the needs of treatment. The existing antifungal drugs are mainly polyenes, azoles, allylamines and the newly developed echinocandins. Considering that the existing antifungal drugs have narrow antibacterial spectrum, high toxicity, drug resistance, etc., new and more ide...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C07D403/12C07D401/14C07D409/14C07D417/14C07D417/12A61K31/4439A61K31/506A61K31/497A61K31/501A61P31/10
CPCC07B2200/13C07D401/12C07D401/14C07D403/12C07D409/14C07D417/12C07D417/14
Inventor 王倩朱圣千李晶晶梅帅君
Owner 王倩
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