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1, 3, 4-oxadiazole-ciprofloxacin heterozygote as well as preparation method and application thereof

A technology of ciprofloxacin and hybrid, which is applied in the field of antibacterial and can solve the problems of increased bacterial resistance

Pending Publication Date: 2021-03-12
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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  • 1, 3, 4-oxadiazole-ciprofloxacin heterozygote as well as preparation method and application thereof
  • 1, 3, 4-oxadiazole-ciprofloxacin heterozygote as well as preparation method and application thereof
  • 1, 3, 4-oxadiazole-ciprofloxacin heterozygote as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1-Cyclopropyl-6-fluoro-7-(4-((5-(furan-2-yl)-1,3,4-oxadiazol-2-yl)methyl)piperazin-1-yl )-4-oxy-1,4-dihydroquinoline-3-carboxylic acid (IIa) preparation steps:

[0028]

[0029] 8.0 mmol of furan-2-carboxyhydrazide, 9.6 mmol of chloroacetyl chloride and 30 mL of ethyl acetate were added to a 100 mL flask, and the reaction was stirred at room temperature for 3 hours. After the reaction was completed, the mixture was filtered and air-dried to obtain the precursor compound. 4.8 mmol of the precursor compound, 9.4 mmol of phosphorus oxychloride, and 20 mL of acetonitrile were added to a 100 mL flask, and the reaction was stirred at 70 ° C for 20 hours. After the reaction was completed, the acetonitrile was removed by concentration under reduced pressure, and 25 mL of ethyl acetate was added to dissolve, and the same volume was used in turn. water, saturated sodium bicarbonate solution and saturated sodium chloride solution were extracted, the organic phase was dried with...

Embodiment 2

[0032] 1-Cyclopropyl-6-fluoro-7-(4-((5-(3-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)methyl)piperazin-1-yl )-4-oxy-1,4-dihydroquinoline-3-carboxylic acid (IIb) preparation steps:

[0033]

[0034] 8.0 mmol of 3-hydroxybenzoic hydrazide, 9.6 mmol of chloroacetyl chloride, and 30 mL of ethyl acetate were added to a 100 mL flask, and the reaction was stirred at room temperature for 3 hours. After the reaction was completed, filtered and air-dried to obtain the precursor compound. 4.8 mmol of the precursor compound, 9.4 mmol of phosphorus oxychloride, and 20 mL of acetonitrile were added to a 100 mL flask, and the reaction was stirred at 70 °C for 12 hours. After the reaction was completed, the acetonitrile was removed by concentration under reduced pressure, and 25 mL of ethyl acetate was added to dissolve it. water, saturated sodium bicarbonate solution and saturated sodium chloride solution were extracted, the organic phase was dried with anhydrous sodium sulfate, and then spin-dri...

Embodiment 3

[0037] 1-Cyclopropyl-6-fluoro-7-(4-((5-(4-hydroxyphenyl)-1,3,4-oxadiazol-2-yl)methyl)piperazin-1-yl )-4-oxy-1,4-dihydroquinoline-3-carboxylic acid (IIc) preparation steps:

[0038]

[0039] 8.0 mmol of 4-hydroxybenzoic hydrazide, 9.6 mmol of chloroacetyl chloride, and 30 mL of ethyl acetate were added to a 100 mL flask, and the reaction was stirred at room temperature for 3 hours. After the reaction was completed, filtered and air-dried to obtain the precursor compound. 4.8 mmol of the precursor compound, 9.4 mmol of phosphorus oxychloride, and 20 mL of acetonitrile were added to a 100 mL flask, and the reaction was stirred at 70 ° C for 20 hours. After the reaction was completed, the acetonitrile was removed by concentration under reduced pressure, and 25 mL of ethyl acetate was added to dissolve, and the same volume was used in turn. water, saturated sodium bicarbonate solution, saturated sodium chloride solution extraction, after the organic phase was dried with anhydrou...

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Abstract

The invention discloses a 1, 3, 4-oxadiazole-ciprofloxacin heterozygote as well as a preparation method and application thereof. The structural formula of the 1, 3, 4-oxadiazole ciprofloxacin heterozygote is shown as a formula (II). A series of 1, 3, 4-oxadiazole-ciprofloxacin heterozygotes with brand-new structures are designed and synthesized by introducing an antibacterial pharmacophore intermediate (I) to a nitrogen atom of a ciprofloxacin C-7 piperazinyl group, and the preparation method comprises the following steps of by taking hydrazide compounds and chloroacetyl chloride as raw materials, carrying out elimination reaction to obtain a precursor compound, carrying out ring-closure reaction on a precursor compound in the presence of phosphorus oxychloride to obtain an intermediate (I), and carrying out reaction on the intermediate (I) and ciprofloxacin to obtain the 1, 3, 4-oxadiazole-ciprofloxacin heterozygote (II). The heterozygote shows antibacterial activity, particularly hasgood 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 1,3,4-oxadiazole-ciprofloxacin hybrid with a new structure and a preparation method and application thereof. Background technique [0002] After more than 50 years of development, fluoroquinolones have become the most widely used broad-spectrum, high-efficiency, low-toxicity first-line anti-infective chemotherapeutics after cephalosporins. However, with the widespread use and even abuse of such drugs, bacterial resistance has increased year by year, which has become a thorny problem worldwide. Therefore, it is of great significance to research and develop novel fluoroquinolone antibacterial agents that are effective against drug-resistant bacteria. SUMMARY OF THE INVENTION [0003] The first object of the present invention is to provide an antibacterial 1,3,4-oxadiazole-ciprofloxacin hybrid or a pharmaceutically acceptable salt th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/12A61K31/496A61P31/04
CPCA61P31/04C07D413/12Y02A50/30
Inventor 杨平谢小保施庆珊
Owner GUANGDONG INST OF MICROBIOLOGY GUANGDONG DETECTION CENT OF MICROBIOLOGY
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