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Substituted phenoxy oxygen alkylamine triazole alcohol antimycotic compounds and method of preparing the same

A technology of phenoxyalkylamine triazole alcohol and compound, which is applied in antifungal agents, organic chemistry, and pharmaceutical formulations, etc.

Inactive Publication Date: 2009-04-08
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no 1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-(N-substituted phenoxyalkylamino )-2-propanol compounds and their antifungal activities

Method used

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  • Substituted phenoxy oxygen alkylamine triazole alcohol antimycotic compounds and method of preparing the same
  • Substituted phenoxy oxygen alkylamine triazole alcohol antimycotic compounds and method of preparing the same
  • Substituted phenoxy oxygen alkylamine triazole alcohol antimycotic compounds and method of preparing the same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0108] Embodiment 1: the preparation of bromobutylphenol ether (II)

[0109] Add 43.18g (0.20mol) of 1,4-dibromobutane, 20.73g (0.15mol) of anhydrous potassium carbonate and 100mL of DMF into a 250mL three-necked flask, and add 50mL of DMF solution containing 9.41g of phenol dropwise , after stirring at room temperature for 2 h, the temperature was raised to 70° C., and the stirring reaction was continued for 3 h. After the reaction, filter, dilute the filtrate with 200 mL of ethyl acetate, wash with water (100 mL×3), dry the organic layer with anhydrous sodium sulfate, filter, evaporate the solvent to dryness, and purify the residue by column chromatography (developing solvent: petroleum ether) , to obtain 21.54 g of a colorless transparent oil, with a yield of 94.0%.

[0110] Other type II compounds were obtained by reacting differently substituted phenols with 1,n-dibromoalkanes of different lengths, and repeating the steps in Example 1.

Embodiment 2

[0111] Embodiment 2: the preparation of N-methyl-N-phenoxybutylamine (III)

[0112] In a 100mL round-bottomed flask, add 50mL of methylamino alcohol solution, dropwise add 20mL of ethanol solution containing 5.73g (0.025mol) of bromobutylphenol ether (II) to it, stir and react at room temperature for 12h, and the reaction is almost complete . After the reaction, the solvent was evaporated to dryness to obtain a white solid, which was used in the next reaction without purification.

[0113] Other III compounds were prepared by repeating the steps in Example 2 by performing substitution reactions with different bromoalkyl substituted phenol ethers (II) and methanol solution.

Embodiment 3

[0114] Embodiment 3: the preparation of N-phenoxypropyl piperazine (III)

[0115] In a 50ml round bottom flask, add 20ml of ethanol, 2.94g (0.011mol) of anhydrous piperazine, 2.08g (0.015mol) of anhydrous potassium carbonate, and dropwise add 2.94 pieces of 4-bromopropylphenol ether into it under stirring. (0.01mol) ethanol solution in 20ml, react at 70°C for 4h. After the reaction, evaporate the solvent to dryness, dissolve the obtained solid with 20ml of ethyl acetate, wash with 20ml*3 water, dry the organic layer, filter, and evaporate the solvent to obtain 1.95g of light yellow solid with a yield of 65.22%. Can be used for the next reaction.

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Abstract

The invention provides a novel highly-efficient, low-toxic, broad-spectrum antifungal azole alcohole compound to substitute for phenoxyalkylamine triadimenol compounds, namely1-(1H-1,2,4- triazole-1-group)-2-(2,4-difluoro phenyl)-3-(N-substitute for phenoxyalkylamine)-2-propanol compounds (including racemic body and R or S type isomer of the compounds) and hydrochloride, nitrate, hydrobromide andmethane sulphonate of the compounds, and a preparation method thereof. The compound has strong antifungal effect on various funguses in shallow and deep parts. Compared with the prior antifungal medicines applied in clinical practice, the compound has the advantages of high efficiency, low toxin and broad antifungal spectrum, and can be used for preparing novel antifungal medicines.

Description

technical field [0001] The invention relates to the field of medical technology, and is a novel triazole alcohol antifungal compound——1-(1H-1,2,4-triazol-1-yl)-2-(2,4-difluoro Phenyl)-3-(N-substituted phenoxyalkylamino)-2-propanol compounds and their salts and preparation methods. Background technique [0002] In recent years, with the extensive application of broad-spectrum antibiotics, antineoplastic drugs, and immunosuppressants, the widespread implementation of radiotherapy and organ transplantation, the widespread development of catheters and intubations, and the rapid increase in immunocompromised patients, especially AIDS patients, have resulted in Fungal infections, especially deep fungal infections, have risen sharply, and deep fungal infections have become the main cause of death from major diseases such as AIDS and tumors. However, as far as the antifungal drugs in clinical use are concerned, there are problems such as large side effects, narrow antibacterial spe...

Claims

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Application Information

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IPC IPC(8): C07D249/08A61K31/496A61K31/4196A61P31/10
Inventor 张万年盛春泉王文雅车晓颖缪震元姚建忠张晶郭巍徐玉兰董国强
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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