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Azole antifungal compound and preparation method and application thereof

A compound, the technology of triazole alcohol, which is applied in the field of medicine and achieves the effects of simple preparation method, high yield and good antifungal activity

Inactive Publication Date: 2013-08-28
NANJING GENERAL HOSPITAL NANJING MILLITARY COMMAND P L A
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far no 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[4-(((5-aryl-1,3,4-oxadiazole- 2-yl)-thio)-methyl)-1 H Report on Antifungal Activity of -1,2,3-Triazol-1-yl]-2-ol Compounds

Method used

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  • Azole antifungal compound and preparation method and application thereof
  • Azole antifungal compound and preparation method and application thereof
  • Azole antifungal compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A new class of triazole alcohol compounds provided by the invention has a structure as shown in the general formula:

[0036]

[0037] Where X is CH=CH, O;

[0038] wherein R is selected from alkyl, halogen, alkoxy or nitro.

[0039] i. Alkyl, 1-5 carbon atoms of alkyl or haloalkyl, wherein the substituents can be located at the ortho, meta, or para positions of the aromatic ring, and can be mono-substituted or multi-substituted.

[0040] ii. Halogen, the substituent is selected from F, CI, Br, I, and can be located at the ortho, meta, or para position of the aromatic ring, and can be mono-substituted or multi-substituted.

[0041] iii. An alkoxy group with 1-2 carbon atoms, where the substituents can be located at the ortho, meta, or para positions of the aromatic ring, and can be mono-substituted or multi-substituted.

[0042] iv. The nitro group can be located at the ortho, meta or para position of the aromatic ring, and can be mono-substituted or multi-substitu...

Embodiment 2

[0081] The intermediate is synthesized according to the reaction scheme of a).

[0082] (1) Preparation of 2-chloro-2',4'-difluoroacetophenone

[0083] Put 200g (1.494mol) of anhydrous aluminum oxide and 150g (1.30mol) of m-difluorobenzene into a 1000mL three-necked bottle, stir at room temperature, slowly add 150g (1.30mol) of chloroacetyl chloride dropwise, and continue to Stir at room temperature for 30 minutes, slowly raise the temperature to 45°C, continue stirring at this temperature for 4.5 hours, pour the reaction solution into ice water as usual, precipitate solids, filter; the filtrate is extracted twice with 800 mL of dichloromethane, and combined Dichloromethane extract, washed with water until neutral, dried over anhydrous sodium sulfate, filtered, and the solvent was recovered to obtain a solid, which was combined twice and recrystallized with ethanol to obtain 2-chloro 2',4'-difluoroacetophenone 215g, yield 88.2%, melting point: 46-47°C.

[0084] (2) Prepa...

Embodiment 3

[0091] The intermediate is synthesized according to the reaction route b), taking 4-chlorobenzoic acid as an example.

[0092] (5) Preparation of methyl 4-chlorobenzoate

[0093] Add 5g (31.9mmol) of 4-chlorobenzoic acid and 25ml of thionyl chloride to a 100ml eggplant-shaped bottle, heat to reflux for 4 hours, evaporate the solvent to dryness under reduced pressure to obtain 4-chlorobenzoyl chloride, dilute it with 15ml of dichloromethane, Add it dropwise to 20ml of methanol under ice-bath conditions. After the dropwise addition, react at room temperature for 2 hours. After the reaction, evaporate to dryness under reduced pressure to obtain 4.46g of light yellow solid methyl 4-chlorobenzoate, with a yield of 83%;

[0094] (6) Preparation of 4-chlorobenzohydrazide

[0095] Add 2.43g (14.2mmol) of methyl 4-chlorobenzoate and 25ml of methanol into a 100ml eggplant-shaped bottle, and slowly add 15ml of hydrazine hydrate solution dropwise at room temperature. solvent, and th...

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Abstract

The present invention relates to a novel triazole alcohol compound. The triazole alcohol compound has a following chemical structural formula as shown in a chemical structure in the specification, wherein X is CH=CH or O; R is selected from alkyl, halogen, alkoxy or nitryl. The invention has the advantages that: the compound has good antifungal activity for various superficial and deep fungi, has the advantages of high efficiency, low toxicity and wide antifungal spectrum compared with conventional clinical applied antifungal drugs, and can be used in the preparation of antifungal drugs. The compound is simple in the preparation method, high in yield, and good in antifungal effect, and a novel compound is provided for the preparation of antifungal drugs.

Description

technical field [0001] The present invention relates to the technical field of medicine, specifically, it is a new class of azole antifungal compounds, i.e. 1-(1 H -1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[4-(((5-aryl-1,3,4-oxadiazole- 2-yl)-thio)-methyl)-1 H -1,2,3-triazol-1-yl]-2-alcohol compounds, and their preparation methods and applications. . Background technique [0002] In recent years, with the wide application of broad-spectrum antibiotics, corticosteroids and immunosuppressants, the promotion of advanced diagnosis and treatment techniques such as organ transplantation, the prevalence of AIDS, and the influence of tumor radiotherapy and chemotherapy, fungal infections, especially deep fungal infections, have become more serious. The magnitude has risen, and deep fungal infection has become the main cause of death from major diseases such as AIDS and tumors. Correspondingly, there are few types of antifungal drugs used in clinical practice, with large adve...

Claims

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Application Information

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IPC IPC(8): C07D413/14A61K31/4245A61P31/10
Inventor 王曙东任海祥汤淏苏华孟庆国张雷俞世冲吴秋业
Owner NANJING GENERAL HOSPITAL NANJING MILLITARY COMMAND P L A
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