Acrylketone derivative of pefloxacin and preparation method and application of acrylketone derivative

A technology of pefloxacin and acrylone, which is applied in the field of drug synthesis, can solve problems such as the uncertainty of the effect of the C-3 carboxyl group of fluoroquinolones, and achieve the effects of increasing anti-tumor activity and drug resistance, and reducing toxic and side effects

Active Publication Date: 2020-09-11
HENAN UNIVERSITY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented inventive chemical entity describes two ways for combining certain molecules together into something that works better than each other or even more efficiently. These methods involve modifying specific parts of these molecule's structure by adding another part called chloroquine (CQ) instead of just one atom from it. By doing this, they enhances their effectiveness against tumors while reducing its harmfulness towards healthy tissues. Overall, this technology allows scientists to creatively design novel medications with improved properties without causing negative reactions like those previously discussed.

Problems solved by technology

This patents discusses finding novel ways to treat patients who may become infected from various types of microorganisms like staphrotococcaceae, pseudonoxanthellae, gram negative bactamims, tuberculosis, pneumonia, necrotropic sinus disease, streptomyces dysgenacea, rheumatoid arthritis, pyoderma ganglia, listeriocephalosporium, nystagric acid resistant enteropathogenesis caused by certain organism called Helvotaxelimycini B complex.

Method used

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  • Acrylketone derivative of pefloxacin and preparation method and application of acrylketone derivative
  • Acrylketone derivative of pefloxacin and preparation method and application of acrylketone derivative
  • Acrylketone derivative of pefloxacin and preparation method and application of acrylketone derivative

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Experimental program
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Effect test

Embodiment 1

[0032] 1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-3-cinnamoyl-quinoline-4(1 H )-ketone (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 pefloxacin shown in formula II as raw material, reacting with carbonyldiimidazole (CDI) to prepare norfloxacin imidazole amide compound shown in formula III, the specific preparation method is as follows:

[0037]

[0038] Take 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4(1 H 20 g (60.0 mmol) of )-keto-3-carboxylic acid II was dissolved in 500 mL of anhydrous acetonitrile, 15.2 g (94.0 mmol) of carbonyldiimidazole was added, and the mixed reactant was stirred and refluxed in a water bath until the raw material II disappeared. 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 yield of 83.5% and m.p. 232...

Embodiment 2

[0047] 1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-3-(4-methoxycinnamoyl)-quinoline-4(1 H )-ketone (I-2), its chemical structural formula is:

[0048]

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

[0050] The preparation method of this compound is:

[0051] (1) 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-1-yl-quinoline-4(1 H )-keto-3-ethanone V is prepared with reference to steps (1)-(3) of implementation 1, the solvent in step (1) is replaced by tetrahydrofuran solution, and the molar ratio of pefloxacin to carbonyldiimidazole is 1:1.0;

[0052] (2) Take 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4(1 H 1.0 g (3.0 mmol) of )-keto-3-ethanone V 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 reactant was refluxed for 20 h, left at room temperature, and the resulting solid was collected by filtration and recrystallized from absolute ethanol to obtain ...

Embodiment 3

[0054] 1-Ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-3-(3,4-dioxymethylenecinnamoyl)-quinoline-4(1 H )-ketone (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:

[0058] (1) 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-1-yl-quinoline-4(1 H )-ketone-3-ethanone V is prepared with reference to steps (1)-(3) of Implementation 1, the solvent in step (1) is replaced by dioxane solution, the mixture of pefloxacin and carbonyldiimidazole The molar ratio is 1:2;

[0059] (2) Take 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4(1 H )-keto-3-ethanone V1.0 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). The mixed reactants were refluxed for 20 h, left at room temperature, and the resulting solid was collected by filtration and recrystallized from absolute...

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Abstract

The invention belongs to the field of medicine synthesis, and relates to a derivative of pefloxacin, in particular to an acrylketone derivative of pefloxacin and a preparation method and application of the acrylketone derivative. The derivative of pefloxacin has the following structural general formula (I): in the formula I, Ar is any one of a benzene ring, a substituted benzene ring, a furan ringor a pyridine ring. According to the acrylketone derivative of pefloxacin, the fluoroquinolone skeleton and the propenone skeleton are effectively spliced, so that a novel fluoroquinolone chalcone-like compound is constructed, the anti-tumor activity and the anti-drug resistance of the novel compound are improved, the toxic and side effects on normal cells are reduced, and the novel fluoroquinolone chalcone-like compound can be used as an anti-tumor active substance to develop an anti-tumor drug with a brand-new structure.

Description

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Claims

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Application Information

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Owner HENAN UNIVERSITY
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