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Furanone ether derivative and preparation method thereof, and application of furanone ether derivative in antibacterial agent

A technology of furanone ethers and derivatives, applied in antibacterial drugs, organic chemistry, etc., can solve problems such as loss of life, and achieve the effects of high activity, good transmission in the body, and good inhibition and killing effects

Inactive Publication Date: 2014-05-07
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Although antibiotics once reduced the serious threat of pathogenic bacteria to human beings, with the emergence of drug-resistant bacteria, people have to face again that more than one-third of the world's people are susceptible to such bacteria infections, and thus lose their lives. dire situation of life

Method used

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  • Furanone ether derivative and preparation method thereof, and application of furanone ether derivative in antibacterial agent
  • Furanone ether derivative and preparation method thereof, and application of furanone ether derivative in antibacterial agent
  • Furanone ether derivative and preparation method thereof, and application of furanone ether derivative in antibacterial agent

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Example 1: Preparation of 4-(3-(diethylamine)propoxy)-3-(4-methoxyphenyl)furan-2(5H)-one (Compound 1)

[0020]

[0021] Dissolve 5mmol of p-methoxyphenylacetic acid and 15mmol of sodium ethylate in 50mL of absolute ethanol, add 10mmol of ethyl bromoacetate at room temperature, raise the temperature to 45°C and react for 10h (detected by TLC). After the reaction, filter with suction and concentrate to One-tenth of the original volume, diluted with 50mL ether, washed 3 times with 30mL water (10mL each time), washed the organic layer with saturated brine until neutral, dried, concentrated, separated by silica gel column chromatography, and the eluent was petroleum ether The mixed solution with a volume ratio of 10:1 to ethyl acetate was concentrated; the anhydrous tetrahydrofuran solution containing 3 mmol of the obtained product was dropped into anhydrous tetrahydrofuran containing 3 mmol of sodium hydride at room temperature, and the dropwise reaction was completed at ...

Embodiment 2

[0022] Embodiment two: the antibacterial activity of compound

[0023] Bacteria were suspended in MH medium at a concentration of approximately 10 5 cfu / mL, the bacterial solution was added to a 96-well plate (100 μL of bacterial solution per well), the culture medium was used as a blank control, DMSO was used as a negative control instead of the test substance, and kanamycin was used as a positive control. Dissolve the test substance in DMSO to make 1600, 800, 400, 200, 100, 50 μg / mL solutions respectively (for MIC 50 If it is less than 5 μg / mL, in further experiments, the prepared concentration gradient is 100, 50, 25, 12.5, 6.25 μg / mL), and added to the 96-well plate in an amount of 11 μL per well [the final concentration of the drug solution is 160 , 80, 40, 20, 10, 5 μg / mL (10, 5, 2.5, 1.25, 0.63 μg / mL for the latter)], four parallel experiments were done for each concentration gradient. Place the 96-well plate in an incubator at 37°C for 24 hours, then add 25 μL per we...

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Abstract

The invention relates to a furanone ether derivative, a preparation method of the furanone ether derivative, and an application of the furanone ether derivative in an antibacterial agent. The compound name of the furanone ether derivative is 4-(3-(diethylamine) propyl group)-3-(4-methoxy-phenyl) furan-2(5H)-ketone. The compound provided by the invention shows an excellent effect of inhibiting and killing tested bacteria, the inhibitory activity to the bacillus subtilis is close to that of the positive control kanamycin, the inhibitory activity to the surface staphylococcus is more than that of the positive control kanamycin, and therefore, the compound can be used to prepare an anti-infective drug. A furanone loop is used to replace an acrylic ester part of the lead compound and an enol ether functional group is used to replace an enamine functional group, so that the harmful effect caused by configuration interconversion is avoided; in addition, diethylamine is taken as the material and is introduced into a kinetophore, so that the such functional micromolecule is more likely to become a prodrug, the novel antibacterial compound with higher activity and better in-vivo transmission is designed and synthesized, and a prepration method for the compound is provided.

Description

technical field [0001] The invention relates to a furanone ether derivative, its preparation method and application in antibacterial drugs. Background technique [0002] Although antibiotics once reduced the serious threat of pathogenic bacteria to human beings, with the emergence of drug-resistant bacteria, people have to face again that more than one-third of the world's people are susceptible to such bacteria infections, and thus lose their lives. The dire situation of life. Therefore, human beings' resistance to pathogenic bacteria still needs to rely on the important means of continuously developing new antibacterial drugs. [0003] Studies have shown that acrylate-type enamine has a better inhibitory effect on bacterial growth, and its trans configuration is much more active than the cis configuration. In order to avoid the trans configuration to the cis configuration under acidic conditions and To affect the antibacterial effect, we further modified the enamine comp...

Claims

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Application Information

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IPC IPC(8): C07D307/60A61K31/341A61P31/04
CPCC07D307/60
Inventor 朱海亮肖竹平张飞杨雨顺
Owner NANJING UNIV
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