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3-aryl-4-(2-acyloxy ethyoxyl)-2(5H)-furanone compound and preparation method and application thereof

A technology of acyloxyethoxy and furanone, applied in the application field of preparing antibacterial drugs, can solve the problems of reduced effectiveness, short life cycle and the like, and achieve the effects of high bacteriostatic activity, good inhibition and killing effects

Inactive Publication Date: 2012-10-24
JISHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The most important reason for bacterial (fungal) drug resistance is that bacteria (fungi) have a short life cycle and can adapt to their living environment very quickly. Antibiotics that were very effective 30 years ago are now very effective lowered, and will be lower in the future

Method used

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  • 3-aryl-4-(2-acyloxy ethyoxyl)-2(5H)-furanone compound and preparation method and application thereof
  • 3-aryl-4-(2-acyloxy ethyoxyl)-2(5H)-furanone compound and preparation method and application thereof
  • 3-aryl-4-(2-acyloxy ethyoxyl)-2(5H)-furanone compound and preparation method and application thereof

Examples

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Effect test

Embodiment 1

[0028] Example 1: 3-(4-bromophenyl)-4-[2-(leucyloxy)ethoxy]-2(5 H ) - Preparation of furanone

[0029] Step 1: Dissolve 2.7g (0.04mol) EtONa in 50mL of absolute ethanol, then add 6.45g (0.030mol) p-bromophenylacetic acid, add 5.1mL (0.045mol) ethyl bromoacetate after dissolving, heat up to 40 Between ~50°C, react for 10 hours, add 70 mL of water, extract three times with 200 mL of AcOEt, wash with saturated brine until neutral, dry, concentrate, and purify by silica gel (200-300 mesh) column chromatography (AcOEt:petroleum ether=1:6) , to obtain 7.7 g of ethyl p-bromophenylacetoxyacetate as a colorless oily product, with a yield of 85%.

[0030] Step 2: Take 7.2g (0.024mol) of ethyl p-bromophenylacetoxyacetate, dissolve it in 60mL of anhydrous THF, add 0.57gNaH (0.025mol), stir at room temperature for 5h, after the reaction is complete, add 100mL of water, and use 240mL diethyl ether was extracted three times, the aqueous layer was acidified with 5M hydrochloric acid, and ...

Embodiment 3

[0037] Example 3: Antibacterial Activity of Compounds

[0038] Bacteria were suspended in MH medium at a concentration of approximately 10 5 cfu mL -1 , add the bacterial solution to a 96-well plate (100 μL of bacterial solution per well), use the culture medium as a blank control, use DMSO instead of a test substance as a negative control, use penicillin G as a positive control for Gram-positive bacteria, and use penicillin G as a positive control for Gram-positive bacteria. Kanamycin was used as a positive control for Lambert-negative bacteria, and ketoconazole was used as a positive control for fungi. Dissolve the test substance in DMSO to prepare 1600, 800, 400, 200, 100, 50 μg·mL -1 solution (for MIC 50 Less than 5μg·mL -1 Yes, when carrying out one-step experiment, the prepared concentration gradient is 100, 50, 25, 12.5, 6.25 μg·mL -1 ), added to a 96-well plate at an amount of 11 μL per well [the final concentrations of the drug solution were 160, 80, 40, 20, 1...

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Abstract

The invention discloses a 3-aryl-4-(2-acyloxy ethyoxyl)-2(5H)-furanone compound, which is shown as a structural formula in the specifications. The compound plays a role in suppressing staphylococcus epidermidis, klebsiella pneumonia, novel cryptococcus gattii and the like and can be used for preparing an anti-infection medicament for treating pneumonia, wound suppuration and the like. The invention also discloses a preparation method of the compound.

Description

technical field [0001] The present invention relates to a class of aryl-4-(2-acyloxyethoxy)-2(5 H )-The preparation method of furanone-type compounds and their application in the preparation of antibacterial drugs. technical background [0002] Pathogenic bacteria (fungi) seriously endanger human health. More than one-third of people in the world are susceptible to infection by such bacteria, and more than two million people die from such infections every year. The emergence and use of antibiotics (antibacterial drugs) has saved thousands of lives, and the great success of antibiotics has paralyzed people, so that in the late 1960s, it was said that our existing antibiotics were sufficient to deal with infectious diseases. diseases, there is no need to develop new antibacterial drugs. However, even today, we have not completely defeated infectious diseases, which have become the second leading cause of death in the world. Because bacteria (fungi) are prone to resistance t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/60C07D405/12A61K31/365A61K31/405A61K31/4178A61K31/4025A61P31/04A61P31/10
Inventor 肖竹平张芳彭知云彭密军田启建朱健江旺
Owner JISHOU UNIVERSITY