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A kind of furanone aniline derivative prepared by metronidazole and its preparation method and application in antibacterial drugs

A technology of furanone aniline and its derivatives, applied in antibacterial drugs, organic chemistry, etc., to achieve good inhibitory and killing effects

Inactive Publication Date: 2018-05-18
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While antibiotics once mitigated the threat, the emergence of drug-resistant bacteria has forced a new facet of the dire situation

Method used

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  • A kind of furanone aniline derivative prepared by metronidazole and its preparation method and application in antibacterial drugs
  • A kind of furanone aniline derivative prepared by metronidazole and its preparation method and application in antibacterial drugs
  • A kind of furanone aniline derivative prepared by metronidazole and its preparation method and application in antibacterial drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1: 4-((3,5-dimethoxyphenyl)amino)-3-(2-methyl-5-nitro-1H-imidazol-1-yl)furan-2(5H)- Preparation of Ketone (Compound 1)

[0020]

[0021] Dissolve 5mmol of metronidazole in 100mL of water, add 10mmol of sodium dichromate, stir magnetically to mix evenly, slowly drop in 98% concentrated sulfuric acid, and react at room temperature for 5h (TLC detects the progress of the reaction). After the reaction, dilute NaOH solution Adjust the pH to 9.1, a large amount of solids are produced, filter the solids, adjust the pH of the filtrate to 4.6 with dilute hydrochloric acid, extract 3 times with ethyl acetate, 100 mL each time, take the organic phase, and evaporate all the solvents in vacuo to obtain an intermediate product; Dissolve 3mmol of the above product and 9mmol of sodium ethoxide in 50mL of absolute ethanol, add 6mmol of ethyl bromoacetate at room temperature, raise the temperature to 45°C and react for 10h (TLC detection). After the reaction, filter with sucti...

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. Put the 96-well plate in an incubator at 37°C for 24 h, then add 25 μL per mL of PB...

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Abstract

The invention relates to a furanone aniline derivate prepared from metronidazole, as well as a preparation method and applicable of the furanone aniline derivate in antibacterial drugs. The derivant is named as 4-((3,5-dimethoxy phenyl) amino)-3-(2-methyl-5-nitro-1H-iminazol-1-radical)furan-2(5H)-ketone. The derivant represents a better inhibiting and killing effect on to-be-tested bacteria, the inhibiting activity of bacillus subtilis is close to that of positive control kanamycin, and the inhibiting activity of the staphylococcus epidermidis exceeds that of positive control kanamycin, so that the derivant can be used for preparing anti-infective drugs; the influence due to configuration interconversion is improved by replacing the acrylate part of a lead compound with a furan ketone ring, a metronidazole structure with stronger antimicrobial action is introduced, and on the basis of in-depth study of the structure-function relationship, a novel antibacterial derivate with a higher activity is designed and synthesized, and the preparation method of the derivate is provided.

Description

technical field [0001] The invention relates to a furanone aniline derivative prepared from metronidazole, a preparation method thereof and an application in antibacterial drugs. Background technique [0002] Pathogenic bacteria seriously threaten human health, and more than one-third of people in the world are susceptible to infection by such bacteria, and then lose their lives. Although antibiotics once alleviated this threat, the emergence of drug-resistant bacteria has forced people to face this severe situation again. Therefore, the continuous development of new antibacterial drugs is still an important means for humans to resist pathogenic bacteria. [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 In order to affect the antibacterial effect, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/04A61P31/04
CPCC07D405/04
Inventor 朱海亮肖竹平张飞杨雨顺
Owner NANJING UNIV
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