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N-acylhydrazone-ciprofloxacin heterozygote and preparation method and application thereof

A technology of ciprofloxacin and acyl hydrazone, which is applied in the field of antibacterial and can solve the problems of increasing bacterial resistance and the like

Active Publication Date: 2021-02-12
GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with the widespread use and even abuse of such drugs, bacterial drug resistance has increased year by year and has become a worldwide thorny problem

Method used

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  • N-acylhydrazone-ciprofloxacin heterozygote and preparation method and application thereof
  • N-acylhydrazone-ciprofloxacin heterozygote and preparation method and application thereof
  • N-acylhydrazone-ciprofloxacin heterozygote and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] (E)-1-cyclopropyl-6-fluoro-7-(4-(2-(2,3-difluorobenzylidene)hydrazino-2-oxyethyl)piperazin-1-yl) -4-Oxygen-1,4-dihydroquinoline-3-carboxylic acid (IIa) preparation steps:

[0024]

[0025] Add 5mmol ciprofloxacin, 5mmol ethyl chloroacetate, 50mL N,N-dimethylformamide (DMF), 0.1mol triethylamine into a 100mL flask, stir and react at 100°C for 24 hours, after the reaction is complete, depressurize Most of the solvent was removed by rotary evaporation, cooled, filtered, and the filter residue was washed with methanol and filtered to obtain the precursor compound. Add 2.5mmol of precursor compound, 12.5mmol of hydrazine hydrate, and 10mL of absolute ethanol into a 100mL flask, stir and react at 75°C for 20 hours, cool, filter, wash with ethanol, and air-dry to obtain intermediate I, namely 1-cyclopropyl- 6-fluoro-7-(4-(2-hydrazino-2-oxyethyl)piperazin-1-yl)-4-oxy-1,4-dihydroquinoline-3-carboxylic acid.

[0026] 1.0 mmol of intermediate I (1-cyclopropyl-6-fluoro-7-(4-(2...

Embodiment 2

[0028] (E)-1-cyclopropyl-6-fluoro-7-(4-(2-(2,5-difluorobenzylidene)hydrazino-2-oxyethyl)piperazin-1-yl) -4-Oxygen-1,4-dihydroquinoline-3-carboxylic acid (IIb) preparation steps:

[0029]

[0030] Add 5mmol ciprofloxacin, 5mmol ethyl bromoacetate, 50mL N,N-dimethylformamide (DMF), 0.1mol triethylamine into a 100mL flask, stir and react at 100°C for 24 hours, after the reaction is complete, depressurize Most of the solvent was removed by rotary evaporation, cooled, filtered, and the filter residue was washed with methanol and filtered to obtain the precursor compound. Add 2.5mmol of precursor compound, 12.5mmol of hydrazine hydrate, and 10mL of absolute ethanol into a 100mL flask, stir and react at 75°C for 20 hours, cool, filter, wash with ethanol, and air-dry to obtain intermediate I, namely 1-cyclopropyl- 6-fluoro-7-(4-(2-hydrazino-2-oxyethyl)piperazin-1-yl)-4-oxy-1,4-dihydroquinoline-3-carboxylic acid.

[0031] 1.0 mmol of intermediate I (1-cyclopropyl-6-fluoro-7-(4-(2-...

Embodiment 3

[0033] (E)-1-cyclopropyl-6-fluoro-7-(4-(2-((1E,2E)-3-(furan-2-yl)allylidene)hydrazino-2-oxyl group Preparation steps of ethyl) piperazin-1-yl)-4-oxyl group-1,4-dihydroquinoline-3-carboxylic acid (IIc):

[0034]

[0035] 1.0 mmol of intermediate I (1-cyclopropyl-6-fluoro-7-(4-(2-hydrazino-2-oxyethyl)piperazin-1-yl)-4-oxyl-1 , 4-dihydroquinoline-3-carboxylic acid), 2.0mmol (E)-3-(furan-2-yl)acrolein, and 20mL of absolute ethanol were added to a 100mL flask, stirred and reacted at 60°C for 24 hours, and the reaction After completion, filter, wash with ethanol, and air-dry to obtain the target product (IIc) with a yield of 80%.1 H NMR(400MHz,DMSO)δ15.15(s,1H,-COOH),11.21 and 11.15(s,1H,-NH-CO-is affected by keto-form and enol-form),8.61(s,1H, quinoline),8.06,8.03and 7.75(s,1H,-CH=N-is affected by keto-form and enol-form),7.82 and7.79(d,1H,quinoline),7.75,7.73 and 7.71(m, 1H,furyl),7.54 and 7.52(d,1H,quinoline),6.86(t,1H,furyl),6.69-6.57(m,3H,furyl and allylidene),3.80(s,1H,cy...

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Abstract

The invention discloses an N-acylhydrazone-ciprofloxacin heterozygote and a preparation method and application thereof. The structural formula of the N-acylhydrazone-ciprofloxacin heterozygote is shown as a formula (II). A series of N-acylhydrazone-ciprofloxacin heterozygotes with brand-new structures are designed and synthesized by introducing an antibacterial pharmacophore N-acylhydrazone to thenitrogen atom of a ciprofloxacin C-7 piperazinyl, and the preparation method comprises the following steps: taking ethyl chloroacetate or ethyl bromoacetate and ciprofloxacin as raw materials, carrying out substitution reaction to obtain a precursor compound; reacting the precursor compound with hydrazine hydrate under a heating condition to obtain an N-hydrazide-ciprofloxacin intermediate (I), and reacting the intermediate (I) with aldehyde to obtain the N-acylhydrazone ciprofloxacin heterozygote (II). The heterozygote shows antibacterial activity, particularly has good antibacterial activity on staphylococcus aureus, escherichia coli and pseudomonas aeruginosa, and can be used as an antibacterial candidate compound.

Description

technical field [0001] The invention belongs to the field of antibacterial technology and relates to an antibacterial drug, in particular to a new-structured N-acylhydrazone-ciprofloxacin hybrid and its preparation method and application. Background technique [0002] After more than 50 years of development, fluoroquinolones have become the most widely used first-line anti-infective chemotherapy drugs with broad-spectrum, high efficiency and low toxicity after cephalosporins. However, with the widespread use and even abuse of such drugs, bacterial drug resistance is increasing year by year, which has become a thorny problem worldwide. Therefore, it is of great significance to research and develop novel fluoroquinolone antibacterial agents effective against drug-resistant bacteria. Contents of the invention [0003] The first object of the present invention is to provide an antibacterial N-acylhydrazone-ciprofloxacin hybrid or a pharmaceutically acceptable salt thereof. ...

Claims

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Application Information

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IPC IPC(8): C07D215/56C07D405/12A61P31/04
CPCC07D215/56C07D405/12A61P31/04Y02A50/30
Inventor 杨平谢小保施庆珊
Owner GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
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