A kind of propenone derivative of n-acetyl ciprofloxacin and its preparation method and application

A technology of ciprofloxacin and acetyl group, applied in the field of drug synthesis, can solve the problems such as uncertainty of the effect of fluoroquinolone C-3 carboxyl group, and achieve the effects of increasing anti-tumor activity and resistance to drug resistance and reducing toxic and side effects

Active Publication Date: 2022-01-21
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is uncertain whether the C-3 carboxyl group of fluoroquinolones can be replaced by different groups to obtain the effect

Method used

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  • A kind of propenone derivative of n-acetyl ciprofloxacin and its preparation method and application
  • A kind of propenone derivative of n-acetyl ciprofloxacin and its preparation method and application
  • A kind of propenone derivative of n-acetyl ciprofloxacin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-3-cinnamoyl-quinolin-4(1H)-one (I-1), its chemical structural formula is:

[0033]

[0034] That is, Ar in formula I is phenyl.

[0035] The preparation method of this compound is:

[0036] (1) Using N-acetyl ciprofloxacin shown in formula II as a raw material (commercially purchased), reacting with carbonyldiimidazole (CDI) to prepare the norfloxacin imidazole amide compound shown in formula III, and its specific preparation Methods as below:

[0037]

[0038] Dissolve 20 g (54.0 mmol) of 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid II in 500 Add 15.2 g (94.0 mmol) of carbonyldiimidazole to mL of anhydrous acetonitrile, and mix the reactant in a water bath with stirring and reflux until the raw material II disappears. Leave it at room temperature, collect the resulting solid by filtration, and recrystallize with acetone to obtain a pale yellow crystal formula III with a...

Embodiment 2

[0047] 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-3-(4-methoxycinnamoyl)-quinolin-4(1H)-one (I-2 ), its chemical structure is:

[0048]

[0049] That is, Ar in formula I is p-methoxyphenyl.

[0050] The preparation method of this compound is as follows:

[0051] (1) The preparation of 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-quinolin-4(1H)-one-3-ethanone V refers to the steps of implementation 1 (1)-(3), replace the solvent in step (1) with tetrahydrofuran, and the molar ratio of N-acetylciprofloxacin to carbonyldiimidazole is 1:1.0;

[0052] (2) Take 1.1 g (3.0 mmol ) was dissolved in 20 mL of absolute ethanol, and 0.57 g (4.2 mmol) of 4-methoxybenzaldehyde and base catalyst piperidine (0.1 mL) were added. The mixed reactants were refluxed for 20 h, left at room temperature, and the resulting solid was collected by filtration and recrystallized from absolute ethanol to obtain a pale yellow crystal formula I-2 with a yield of 74.6%, m.p. 232~234°C. 1 H ...

Embodiment 3

[0054] 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-3-(3,4-dioxomethylenecinnamoyl)-quinolin-4(1H)-one (I-3), its chemical structural formula is:

[0055]

[0056] That is, Ar in formula I is 3,4-(dioxymethylene)phenyl.

[0057] The preparation method of this compound is as follows:

[0058] (1) The preparation of 1-cyclopropyl-6-fluoro-7-(4-acetylpiperazin-1-yl)-quinolin-4(1H)-one-3-ethanone V refers to the steps of implementation 1 (1)-(3), replace the solvent in step (1) with dioxane, and the molar ratio of N-acetylciprofloxacin to carbonyldiimidazole is 1:2.0;

[0059] (2) Take 1-ethyl-6,8-difluoro-7-(3,4-dimethylpiperazin-1-yl)-quinolin-4(1H)-one-3-ethanone V1. 1 g (3.0 mmol) was dissolved in 20 mL of absolute ethanol, and 0.53 g (3.5 mmol) of 3,4-dioxymethylene benzaldehyde and base catalyst piperidine (0.1 mL) were added. The mixed reactants were refluxed for 20 h, left at room temperature, and the resulting solid was collected by filtration and recrystalliz...

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Abstract

The invention belongs to the field of drug synthesis, and relates to derivatives of N-acetyl ciprofloxacin, in particular to a propenone derivative of N-acetyl ciprofloxacin and its preparation method and application. It has the following structural formula (I): In the formula, Ar is any one selected from benzene ring, furan ring or pyridine ring and its substituents. A sort of N ‑Acetyl ciprofloxacin's acrylone derivatives have achieved the effective splicing of fluoroquinolone skeleton and acrylone skeleton, and then constructed a new fluoroquinolone "chalcone-like" compound, thereby increasing the antitumor activity of the new compound And anti-drug resistance, and reduce the toxic and side effects on normal cells, it can be used as an anti-tumor active substance to develop anti-tumor drugs with a new structure.

Description

technical field [0001] The invention belongs to the field of drug synthesis and relates to derivatives of N-acetyl ciprofloxacin, in particular to a propenone derivative of N-acetyl ciprofloxacin and its preparation method and application. Background technique [0002] N-acetyl ciprofloxacin belongs to fluoroquinolones, its antibacterial activity in vitro is similar to that of norfloxacin, slightly worse than that of ciprofloxacin, but its antibacterial activity in vivo includes Escherichia coli, pneumoniae bacteria, Pseudomonas aeruginosa and gold Staphylococcus was significantly better than norfloxacin. The mechanism of action is the same as norfloxacin. At present, the drug is mainly used for genitourinary system infection and intestinal infection. As the lead of new drugs, based on the structure or mechanism of N-methyllomefloxacin, research and discovery of new drugs is an effective method for new drug innovation. [0003] The acrylone structure is not only the chara...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/38C07D405/06C07D401/06A61P35/00A61P35/02
CPCC07D215/38C07D405/06C07D401/06A61P35/00A61P35/02
Inventor 黄帅曹玉辉崔红艳胡国强
Owner HENAN UNIVERSITY
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