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Cyprofluoroquinolone C-3-s-triazole thioetherketone thiosemicarbazone compound and its preparation method and application

A technology of azole thioetherketone thiosemicarbazone and cyprofluoroquinolone, which is applied in the field of drug synthesis and can solve the problems of low tumor therapeutic index and high toxicity

Inactive Publication Date: 2017-01-04
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Malignant tumors are major diseases that threaten human life and health. The current clinically used drugs have high toxicity due to poor selectivity and low therapeutic index for tumors. Therefore, it is increasingly urgent to develop anti-tumor drugs with new structures.

Method used

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  • Cyprofluoroquinolone C-3-s-triazole thioetherketone thiosemicarbazone compound and its preparation method and application
  • Cyprofluoroquinolone C-3-s-triazole thioetherketone thiosemicarbazone compound and its preparation method and application
  • Cyprofluoroquinolone C-3-s-triazole thioetherketone thiosemicarbazone compound and its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0046] 2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinolin-4(1H)-one-3-yl]-4H-[1 ,2,4] triazole-3-sulfanyl}-1-acetophenone thiosemicarbazone (I-1), its chemical structural formula is:

[0047]

[0048] That is, R in formula I is a hydrogen atom.

[0049] The preparation method of this compound is: take the intermediate (S)-2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4( 1H)-keto-3-yl]-4H-[1,2,4]triazole-3-thio)-1-acetophenone (VI-1) (2.0g, 3.9mmol) was dissolved in glacial acetic acid ( 20 mL), thiosemicarbazide (0.42 g, 4.7 mmol) was added, and the mixture was refluxed for 6 h. Evaporate the solvent under reduced pressure, add water (30 mL) to dissolve, add 0.1 g of activated carbon and stir at 60 °C for 1 h to decolorize. The filtrate was adjusted to neutral with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water, dried, and recrystallized from absolute ethanol to obtain a light yellow cr...

Embodiment 2

[0051] 2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinolin-4(1H)-one-3-yl]-4H-[1 ,2,4] triazole-3-sulfanyl}-1-(p-methoxyphenyl)-ethanone thiosemicarbazone (I-2), its chemical structural formula is:

[0052]

[0053] That is, R in formula I is p-methoxy.

[0054]The preparation method of this compound is: take the intermediate (S)-2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4( 1H)-keto-3-yl]-4H-[1,2,4]triazole-3-thio)-1-(p-methoxyphenyl)-ethanone (VI-2) (2.0g, 3.6mmol) was dissolved in glacial acetic acid (20mL), thiosemicarbazide (0.37g, 4.0mmol) was added, and the mixture was refluxed for 10h. Evaporate the solvent under reduced pressure, add water (30 mL) to dissolve, add 0.1 g of activated carbon and stir at 60 °C for 1 h to decolorize. The filtrate was adjusted to neutral with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water, dried, and recrystallized from absolute ethanol to obtain ...

Embodiment 3

[0056] 2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinolin-4(1H)-one-3-yl]-4H-[1 ,2,4] triazole-3-sulfanyl}-1-(o-methoxyphenyl)-ethanone thiosemicarbazone (I-3), its chemical structural formula is:

[0057]

[0058] That is, R in formula I is o-methoxy.

[0059] The preparation method of this compound is: take the intermediate (S)-2-{5-[1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)-quinoline-4( 1H)-keto-3-yl]-4H-[1,2,4]triazole-3-thio)-1-(o-methoxyphenyl)-ethanone (VI-3) (2.0g, 3.6mmol) was dissolved in glacial acetic acid (20mL), thiosemicarbazide (0.49g, 5.4mmol) was added, and the mixture was refluxed for 12h. Evaporate the solvent under reduced pressure, add water (30 mL) to dissolve, add 0.1 g of activated carbon and stir at 60 °C for 1 h to decolorize. The filtrate was adjusted to neutrality with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water, dried, and recrystallized from absolute ethanol to obt...

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Abstract

The invention discloses a cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound and a preparation method and application thereof. The chemical general structure of the compound is shown in formula I, in which R is at least one of H, ether group, hydroxyl, methyl, halogeno-group and nitro. According to the cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound disclosed by the invention, a fluoroquinolone framework is actively overlaid or structurally complemented with three different pharmacophores such as a s-triazole heterocyclic ring, thiosemicarbazone and the like, so that the anti-tumor activity of the novel compound is increased, the toxic and side effects of normal cells are reduced, and the compound can serve as an anti-tumor activity matter to develop an anti-tumor drug of a novel structure.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, and in particular relates to a ciprofluoroquinolone C-3-s-triazole thioether ketone thiosemicarbazone compound, and also relates to a ciprofluoroquinolone C-3-s-triazole thioether ketone thiosemicarbazone compound A preparation method of a thiourea compound and its application in the preparation of antitumor drugs. Background technique [0002] Malignant tumors are major diseases that threaten human life and health. The current clinically used drugs have high toxicity due to poor selectivity and low therapeutic index for tumors. Therefore, it is increasingly urgent to develop anti-tumor drugs with new structures. Based on the similarity in sequence and function between the target of antibacterial fluoroquinolones-topoisomerase and the corresponding topoisomerase in mammals, the antibacterial activity of fluoroquinolones can be transformed into antitumor activity through structural modifica...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04C07D405/14A61P35/00
CPCC07D401/04C07D405/14
Inventor 敬永生吴书敏倪礼礼闫强高留州谢玉锁胡国强
Owner HENAN UNIVERSITY
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