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Bis-substituted aryl compounds and application thereof

A double-substitution and compound technology, applied in the field of pharmaceutical compounds, can solve problems such as difficulty in clinical drug selection and increased resistance of fungi to drugs, and achieve the effect of reversing drug resistance and improving sensitivity

Active Publication Date: 2017-06-06
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

However, with the extensive use of antifungal drugs in recent years, the resistance of fungi to drugs has gradually increased.
Strains resistant to fluconazole usually have cross-resistance to other azole drugs, making it difficult to select clinical drugs for the treatment of Candida albicans infection

Method used

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  • Bis-substituted aryl compounds and application thereof
  • Bis-substituted aryl compounds and application thereof
  • Bis-substituted aryl compounds and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0080] Example 1: Preparation of (1E,4E)-1,5-bis(thiophen-2-yl)penta-1,4-dien-3-one

[0081]

[0082] Take acetone (10mmol), add ethanol 20ml, after mixing, slowly add 10% to 50% NaOH aqueous solution (40mmol) and 2-thiophene carboxaldehyde (20mmol) at room temperature, stir at room temperature until the reaction is complete, then pour the reaction solution into 200ml A yellow solid was precipitated in ice water, filtered and dried, and the crude product was recrystallized from ethanol to obtain a yellow solid with a melting point of 116-118°C and a yield of 63%. ESIMS m / z:247.0[M+H] + .

Embodiment 2

[0083] Example 2: Preparation of (1E,4E)-1,5-bis(3,4-dihydroxyphenyl)penta-1,4-dien-3-one

[0084]

[0085] Take acetone (10mmol), add ethanol 20ml, after mixing, slowly add 10% to 50% NaOH aqueous solution (40mmol) and veratraldehyde (20mmol) at room temperature, stir at room temperature until the reaction is complete, then pour the reaction solution into 200ml of ice In water, a yellow solid was precipitated, filtered and dried, and the crude product was recrystallized with ethanol to obtain a yellow solid. After drying, take the yellow solid (1mmol), add 20ml of dry dichloromethane, and slowly add BBr at -15°C 3 (12mmol), after the dropwise addition was completed, it was moved to room temperature and stirred until the reaction was completed, and treated with water, a solid was precipitated, filtered, dried, and the crude product was recrystallized with ethanol to obtain a red solid. ESIMS m / z:299.1[M+H] + .

Embodiment 3

[0086] Example 3: Preparation of 2,5-bis((E)-3,4-dihydroxybenzylidene)cyclopentan-1-one

[0087]

[0088] Take cyclopentanone (10mmol), add 20ml of ethanol, after mixing, slowly add 10% to 50% NaOH aqueous solution (40mmol) and veratraldehyde (20mmol) at room temperature, stir at room temperature until the reaction is complete, then pour the reaction solution into In 200ml of ice water, the yellow solid precipitated was filtered and dried, and the crude product was recrystallized with ethanol to obtain a yellow solid. After drying, the yellow solid (1mmol) was taken, and 20ml of dry dichloromethane was added, and BBr was slowly added dropwise at -15°C. 3 (12mmol), after the dropwise addition was completed, it was moved to room temperature and stirred until the reaction was completed, treated with water, and a solid was precipitated, filtered, dried, and the crude product was recrystallized with ethanol. ESIMS m / z:325.9[M+H] + .Example 4: Preparation of 2,5-bis((E)-3,4-dihy...

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PUM

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Abstract

The invention relates to bis-substituted aryl compounds and application thereof. The structure of the bis-substituted aryl compounds is disclosed as Formula I, II or III. The experimental verification detects that the bis-substituted aryl compounds can be combined with azole antifungal drugs to enhance the sensitivity of drug-resistant fungi to azole drugs and implement drug resistance reversion. Therefore, the invention provides a new way for clinical treatment of drug-resistant fungi.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical compounds, in particular to a disubstituted aryl compound and its application in the preparation of antifungal and synergistic antifungal drugs. Background technique [0002] Mycoses are diseases caused by fungi. As a class of eukaryotic organisms that widely exist in nature, fungi can infect different parts of the human body. From the perspective of clinical pathogenicity, mycoses can be divided into two categories: superficial mycosis and deep mycosis. Many problems, such as the abuse of antibiotics, lead to certain damage to the normal flora symbiotic relationship between bacteria and fungi; secondly, more and more organ transplant operations are carried out clinically, and the use of postoperative immunosuppressants affects the normal function of the body. Immunity function reduces the body's resistance to fungi. The above problems have made the incidence of fungal infections in deep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/22C07C49/248C07C49/747C07D405/14C07D213/68C07D409/14C07D261/08C07D307/52C07D231/12A61K31/381A61K31/12A61K31/122A61K31/4525A61K31/45A61K31/4535A61K31/341A61K31/42A61K31/415A61K31/4196A61P31/10
CPCA61K31/12A61K31/122A61K31/341A61K31/381A61K31/415A61K31/4196A61K31/42A61K31/45A61K31/4525A61K31/4535C07C49/248C07C49/747C07D213/68C07D231/12C07D261/08C07D307/52C07D333/22C07D405/14C07D409/14A61K2300/00
Inventor 金永生董怀怀王元花彭雪米姚淞允赵菲张大志姜远英
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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