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 reduced antibacterial efficacy of antibiotics, drug resistance, difficulty in clinical treatment, etc., and achieves inhibition of bacterial biofilm formation, simple manufacturing process, The effect of broad application prospects

Inactive Publication Date: 2009-08-12
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented inventions involve designing and creating novel molecule classes for use against bacteria's growth without causing them becoming resistant due to their ability to form biological films on surfaces like teeth. These small organic molecular structures prevent bacterium from forming over time by acting together specifically at certain sites within cells called quaternary ammoniums (QA) which act as binding agents between DNA strands during cell division. By combining this type of structure with other types of substances such as enzyme substrates, we aimed towards developing more effective ways to fight off microorganisms caused by existing treatments.

Problems solved by technology

There were previous attempts at identifying chemical structures called quaternary salts like azalide chemistry, including certain types of substances known collectively as pseudoflagellins. These include hydroxymodels, pyrochromatols, chlorophyllanes, carboxylate estrates, nitrosothiolate type peptasis agents, tannoids, cyclooxane stems, and others. However, these methods did not always work well due to limitations associated with existing techniques involving organisms' defense mechanisms against harmful environmental strains caused by gram negative rodsponding to specific enzyme systems involved in cellular processes.

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] 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) intermediate product-synthesis of 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 represented by formula (IX), the Chinese name is 5-hydroxy-3,4-dibromo-2(5H)-furanone, and the yield is 65.1%.

...

Embodiment 2

[0054] Synthesis of halogenated furanone compounds 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) Intermediate product—synthesis of 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 re...

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 )δ 3.60(s, 3H), 5.78(s, 1H); MS(ESI): m / z 183(M+H) + , 205.1(M+Na) + .

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

[00...

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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

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Claims

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Application Information

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Owner JINAN UNIVERSITY
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