3-aryl-4-arylamino-2 (5(i)H(/i))-furanone compounds as well as preparation method and application thereof

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

Inactive Publication Date: 2011-04-06
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-arylamino-2 (5(i)H(/i))-furanone compounds as well as preparation method and application thereof
  • 3-aryl-4-arylamino-2 (5(i)H(/i))-furanone compounds as well as preparation method and application thereof
  • 3-aryl-4-arylamino-2 (5(i)H(/i))-furanone compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: 3-(4-bromophenyl)-4-(4-nitroanilino)furan-2(5 H ) - Preparation of ketones

[0033] Step 1. Dissolve 0.9g of EtONa in 50mL of absolute ethanol, then add 2.15g of p-bromophenylacetic acid, add 1.7mL of ethyl bromoacetate after dissolving, heat up to 40-50°C, react for 10h, add 50mL of water, use 200mL AcOEt was extracted three times, washed with saturated brine until neutral, dried, concentrated, and purified by silica gel (200-300 mesh) column chromatography (AcOEt:petroleum ether=1:6) to obtain a colorless oil (p-bromophenylacetoxy ethyl acetate) 2.50g, yield 83%.

[0034] Step 2. Take 2.4g of ethyl p-bromophenylacetoxyacetate, dissolve it in 50mL of anhydrous THF, add 0.19gNaH, stir at room temperature for 5h, after the reaction is complete, add 100mL of water, extract three times with 240mL of ether, and the water layer Acidify with 5mol / L hydrochloric acid, precipitate out, let stand, filter, wash, dry to obtain light yellow solid 3-(4-bromophenyl)-4-hy...

Embodiment 2

[0037] According to the method similar to Example 1, using different substituted forms of aniline and phenylacetic acid as raw materials, furanone-type enamine compounds 1-78 listed in Table 1 were synthesized.

[0038] 3-aryl-4-arylamino-2 (5 H )- each R group of furanone compound

[0039] serial number

[0040] 7

[0041] 54

[0042] Note: The initial raw materials were purchased from aldrich company

Embodiment 3

[0043] Example 3: Antibacterial Activity of Compounds

[0044] 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 gram-positive bacteria as a positive control. 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, 10, 5 μg·mL -1 (10,...

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PUM

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Abstract

The invention discloses 3-aryl-4-arylamino-2 (5(i)H( / i))-furanone compounds, which are characterized in that the compounds have the following structural general formulas: in formula I, if R1=R3=Br, Cl or OCH3 and R2=R4=R5=R6=R8=H, R7=NO2, F, Cl, Br, OCH3 or OH; if R2=F, Cl, Br, OH, NO2 or OCH3 and R1=R3=R4=R5=R6=R8=H, R7=NO2, F, Cl, Br, OCH3 or OH; if R1=R3=Br, Cl or OCH3 and R2=R4=R5=R6=R8=H, R6=NO2, F, Cl, Br, OCH3 or OH; if R2=F, Cl, Br, OH, NO2 or OCH3 and R1=R3=R4=R5=R8=H, R6=R7=OCH3 or OH; and R1=R3=Br, Cl or OCH3 and R2=R4=R5=R8=H, R6=R7=OCH3 or OH. The compounds of the invention have preferable inhibition effects on staphylococcus epidermidis, Klebsiella pneumoniae, Cryptococcus neoformans and the like, and can be used for preparing anti-infective drugs for treating pneumonia, septic wounds and the like. The invention discloses a preparation method of the compounds.

Description

technical field [0001] The present invention relates to a class of 3-aryl-4-arylamino-2 (5 H )-furanone type compounds and their preparation methods 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 to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/66A61K31/365A61P31/04
Inventor 肖竹平彭密军颜文斌欧阳玉祝刘祝祥梁文德刘甜
Owner JISHOU UNIVERSITY
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