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A kind of triazole compound containing alkenyl ether structure and its preparation method and application

A technology of triazoles and compounds, which is applied in the field of medicine, can solve the problems such as the antifungal activity of triazoles compounds that have not been seen, and achieve the effects of environmental friendliness, simple process and easy operation

Active Publication Date: 2014-10-29
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there are no reports of triazole compounds with enyl ether structure and their antifungal activity, so these compounds have great research value in antifungal infection

Method used

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  • A kind of triazole compound containing alkenyl ether structure and its preparation method and application
  • A kind of triazole compound containing alkenyl ether structure and its preparation method and application
  • A kind of triazole compound containing alkenyl ether structure and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The synthetic method of compound 1, comprises the steps:

[0034] (1) Preparation of α-chloro-2,4-difluoropropiophenone (II)

[0035] Put 80g (0.6mol) of anhydrous aluminum trichloride and 60ml (0.6mol) of m-difluorobenzene into a 500ml three-neck flask, stir in a water bath at 10°C, add 60ml (0.6mol) of 2-chloropropionyl chloride dropwise, and add dropwise After completion, the temperature was raised to 40 ° C, and the reaction solution was poured into ice water after maintaining this temperature for 6 h. The aqueous phase was extracted three times with 600 ml of dichloromethane, and the organic phases were combined and washed with 5% NaHCO 3 Wash the organic phase twice with 800ml of aqueous solution, then wash with water to pH 7, dry over anhydrous sodium sulfate, filter to obtain a transparent light yellow liquid, and distill under reduced pressure to obtain 88.5g of light yellow oil, which is the compound α-chloro-2,4 -Difluoropropiophenone, yield 72.1%.

[0036]...

Embodiment 2

[0045] The synthetic method of compound 2, comprises the steps:

[0046] (1) Preparation of α-chloro-2,4-difluoropropiophenone (II)

[0047] Put 147g (1.1mol) of anhydrous aluminum trichloride and 60ml (0.6mol) of m-difluorobenzene into a 500ml three-necked flask, stir in a water bath at 13°C, add 90ml (0.9mol) of 2-chloropropionyl chloride dropwise, and add dropwise After completion, the temperature was raised to 50 ° C, and the reaction solution was poured into ice water after maintaining this temperature for 5 h. The aqueous phase was extracted three times with 600 ml of dichloromethane, and the organic phases were combined and washed with 5% NaHCO 3 Wash the organic phase twice with 800ml of aqueous solution, then wash with water to pH 7, dry over anhydrous sodium sulfate, filter to obtain a transparent light yellow liquid, and distill under reduced pressure to obtain 118.9g of light yellow oil, which is the compound α-chloro-2,4 -Difluoropropiophenone, yield 96.8%.

[0...

Embodiment 3

[0057] The synthetic method of compound 3, comprises the steps:

[0058] (1) Preparation of α-chloro-2,4-difluoropropiophenone (II)

[0059] 253g (1.9mol) of anhydrous aluminum trichloride and 60ml (0.6mol) of m-difluorobenzene were placed in a 500ml three-necked flask, stirred in a water bath at 17°C, 120ml (1.2mol) of 2-chloropropionyl chloride was added dropwise, and After completion, the temperature was raised to 60 ° C, and the reaction solution was poured into ice water after maintaining this temperature for 3.5 h. The aqueous phase was extracted three times with 750 ml of dichloromethane, and the organic phases were combined and washed with 5% NaHCO 3 Wash the organic phase twice with 800ml of aqueous solution, then wash with water to pH 7, dry over anhydrous sodium sulfate, filter to obtain a transparent light yellow liquid, and distill under reduced pressure to obtain 108.4g of light yellow oil, which is the compound α-chloro-2,4 -Difluoropropiophenone, yield 88.3%. ...

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Abstract

The invention provides triazole compounds containing olefine ether structure, and a preparation method and application thereof. The compounds provided by the invention have strong antifungal effects on various fungi, especially shallow fungi. Compared with the existing antifungal drugs used in clinic, the invention has the advantages of high efficiency, low toxicity and wide antifungal spectrum, and can be used for preparing new antifungal drugs. The structural general formula of the triazole compounds is disclosed in the specification, wherein R is F, Cl or Br.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a triazole compound containing an enyl ether structure, a preparation method thereof and an application in antifungal drugs. Background technique [0002] In recent years, due to the abuse of broad-spectrum antibiotics, adrenal cortex hormones, antineoplastic drugs, and immunosuppressants, as well as the impairment of immune system function in patients caused by clinical radiotherapy and chemotherapy, organ transplantation, and surgery, etc., the flora imbalance and the body's response to Fungal resistance is reduced, making fungal infections easier to develop and harder to control. So far, although people have made great progress in the prevention and treatment of fungal infections, there are still big problems. As far as the antifungal drugs currently in clinical use are concerned, there are problems such as large side effects, narrow antibacterial spectrum, and easy drug res...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D249/08A61P31/10
Inventor 胡永红王路路杨文革沈飞徐志远
Owner NANJING TECH UNIV
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