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Cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound and preparation method and application thereof

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: 2015-05-20
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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  • Cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound and preparation method and application thereof
  • Cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound and preparation method and application thereof
  • Cyclopropylfluoroquinolone C-3 s-triazole thioether ketone thiosemicarbazone compound and preparation method and application thereof

Examples

Experimental program
Comparison scheme
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-thio group}-1-acetophenone thiosemicarbazide (I-1), its chemical structural formula is:

[0047]

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

[0049] The preparation method of the compound is as follows: taking 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-sulfanyl}-1-acetophenone (VI-1) (2.0 g, 3.9 mmol) 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. The solvent was evaporated under reduced pressure, water (30 mL) was added to dissolve, 0.1 g of activated carbon was added, and the mixture was stirred and decolorized at 60° C. for 1 h. The filtrate was adjusted to neutrality with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water, dried, and r...

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-thio}-1-(p-methoxyphenyl)-acetone thiosemicarbazide (I-2), its chemical structural formula is:

[0052]

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

[0054]The preparation method of the compound is as follows: taking 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-sulfanyl}-1-(p-methoxyphenyl)-ethanone (VI-2) (2.0 g, 3.6 mmol) was dissolved in glacial acetic acid (20 mL), thiosemicarbazide (0.37 g, 4.0 mmol) was added, and the mixture was refluxed for 10 h. The solvent was evaporated under reduced pressure, water (30 mL) was added to dissolve, 0.1 g of activated carbon was added, and the mixture was stirred and decolorized at 60° C. for 1 h. The filtrate was adjusted to neutrality with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water,...

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-thio}-1-(o-methoxyphenyl)-acetone thiosemicarbazide (I-3), its chemical structural formula is:

[0057]

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

[0059] The preparation method of the compound is as follows: taking 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-sulfanyl}-1-(o-methoxyphenyl)-ethanone (VI-3) (2.0g, 3.6 mmol) was dissolved in glacial acetic acid (20 mL), thiosemicarbazide (0.49 g, 5.4 mmol) was added, and the mixture was refluxed for 12 h. The solvent was evaporated under reduced pressure, water (30 mL) was added to dissolve, 0.1 g of activated carbon was added, and the mixture was stirred and decolorized at 60° C. for 1 h. The filtrate was adjusted to neutrality with concentrated ammonia water, and the resulting solid was collected by filtration, washed with water,...

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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 cyclopropyl fluoroquinolone C-3 s-triazole sulfide ketone thiosemicarbamate compound, and also relates to a cyclopropyl fluoroquinolone C-3 s-triazole sulfide ketal ketal The preparation method of thiourea compound and its application in the preparation of antitumor drugs. Background technique [0002] Malignant tumors are a major disease that threatens human life and health. Currently, drugs in clinical use are highly toxic due to poor selectivity and have a low therapeutic index for tumors. Therefore, it is increasingly urgent to develop antitumor drugs with new structures. Based on the similarity in sequence and function between topoisomerase, the target of antibacterial fluoroquinolone, and the corresponding topoisomerase in mammals, the antibacterial activity of fluoroquinolone can be converted into its antitumor activity through structural modification....

Claims

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Application Information

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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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