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Halogenated furan ketone compound, and use thereof in antiinfective drug preparation

A technology of halogenated furanones and compounds, which is applied to the application field of organic compounds in biomedicine, can solve the problems of difficult clinical treatment, reduced antibacterial efficacy of antibiotics, drug resistance, etc., achieves broad application prospects, inhibits the formation of bacterial biofilms, The effect of simple manufacturing process

Inactive Publication Date: 2012-07-18
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Methicillin-resistant Staphylococcus aureus (MRSA) was first discovered in 1961. Since then, MRSA infections have increased day by day and are resistant to most antibiotics, which has brought great difficulties to clinical treatment.
The antibacterial efficacy of many commonly used antibiotics is decreasing day by day, and bacterial drug resistance has become a difficult problem in the treatment of infectious diseases

Method used

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  • Halogenated furan ketone compound, and use thereof in antiinfective drug preparation
  • Halogenated furan ketone compound, and use thereof in antiinfective drug preparation
  • Halogenated furan ketone compound, and use thereof in antiinfective drug preparation

Examples

Experimental program
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Effect test

Embodiment 1

[0042] The synthesis of halogenated furanone compound shown in embodiment 1 formula (I)

[0043] Synthesis of this embodiment figure 1 The halogenated furanone compound shown in Chinese formula (I), its synthesis method adopts the chemical synthesis method of this field routine, specifically comprises the following steps:

[0044] (1) Synthesis of intermediate product-halogenated furanone compound shown in formula (IX)

[0045] Add 9.6g of freshly steamed furfural and 110mL of water, add 86g of bromine under ice-bath cooling, raise the temperature and reflux for 0.5h, and concentrate under reduced pressure to obtain a light yellow solid; decolorize and recrystallize the light yellow solid with activated carbon to obtain a crude product, which is purified by silica gel column chromatography (V 乙酸乙酯 :V 石油醚 =1:6) to obtain 16.79 g of white solid, which is the compound shown in formula (IX), the Chinese name is 5-hydroxyl-3,4-dibromo-2(5H)-furanone, and the yield is 65.1%.

[...

Embodiment 2

[0054] Synthesis of halogenated furanone compound shown in embodiment 2 formula (II)

[0055] Synthesis of this embodiment figure 1 The halogenated furanone compound shown in Chinese formula (II), its synthesis method adopts the conventional chemical synthesis method in this field, specifically comprises the following steps:

[0056] (1) Synthesis of intermediate product-compound shown in formula (IX)

[0057] The synthesis steps of the compound shown in formula (IX) are the same as in Example 1.

[0058] (2) When R=Me, the synthesis of final product 3,4-dibromo-5-methoxy-2(5H)-furanone

[0059] Dissolve 6.45g of the compound represented by the above formula (IX) in 11mL of methanol, add 1mL of concentrated sulfuric acid, reflux for 5h; cool to room temperature, add 60mL of water to quench the reaction, extract with benzene (60mL×3); then use 120mL of saturated Washed with sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and concentrated under red...

Embodiment 3

[0067] Synthesis of halogenated furanone compound shown in embodiment 3 formula (III)

[0068] Synthesis of this embodiment figure 1 The halogenated furanone compound shown in Chinese formula (III), its synthesis method adopts the chemical synthesis method conventional in this field, specifically comprises the following steps:

[0069] (1) When R=Me, the synthesis of 3,4-dichloro-5-methoxy-2(5H)-furanone

[0070] 4.23g of mucic acid was dissolved in 11mL of methanol, 1mL of concentrated sulfuric acid was added, and the reaction was refluxed for 5h; the follow-up treatment was the same as the operation when R=Me in Example 2, and finally 2.36g of colorless liquid was obtained, with a yield of 51.6%. The colorless liquid is 3,4-dichloro-5-methoxy-2(5H)-furanone, numbered as compound 9.

[0071] 1 H NMR (300MHz, CDCl 3 )δ3.60(s, 3H), 5.78(s, 1H); MS(ESI): m / z183(M+H) + , 205.1(M+Na) + .

[0072] (2) When R=Et, the synthesis of 3,4-dichloro-5-ethoxyl-2(5H)-furanone

[0073...

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Abstract

The invention discloses a halogenated furanone compound and the application thereof in preparing anti-infective drugs. The structural formula of the halogenated furanone compound is indicated by the formula (I), II), (III), (IV), (V), (VI), (VII) or (VIII). The halogenated furanone compound designed and synthesized by the invention has good effect in inhibiting the formation of bacterial biomembranes, can be used as a bacterial biomembrane inhibitor, is separately used or used together with antibiotic drug to overcome the problem of clinical antibiotic resistance.

Description

technical field [0001] The invention relates to the application of organic compounds in biomedicine, in particular to a halogenated furanone compound and its application in the preparation of anti-infective drugs. Background technique [0002] Methicillin-resistant Staphylococcus aureus (MRSA) was discovered for the first time in 1961. Since then, MRSA infections have been increasing and are resistant to most antibiotics, which has brought great difficulties to clinical treatment. The antibacterial efficacy of many commonly used antibiotics is decreasing day by day, and bacterial drug resistance has become a difficult problem in the treatment of infectious diseases. [0003] Bacterial biofilms are structural, coordinated, and functional highly organized groups whose formation has been found to be an important factor in antibiotic resistance. Modern studies have found that clinical infections related to bacterial biofilms are increasing. According to reports, 80% of human ba...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/58C07D307/60C07D207/44A61K31/365A61K31/4015A61P31/04
Inventor 陈卫民程超孙平华宋秋玲王玉真
Owner JINAN UNIVERSITY
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