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3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings as well as preparation method and application thereof

A technology of ethyl quinoline ring and difluoroquinolone, which is applied in the field of difluoroquinolone derivative compounds, can solve the problems of poor patient tolerance, high toxicity of antitumor drugs, and low cure rate of tumor diseases, so as to reduce toxic side effects and increase Effect of antitumor activity

Inactive Publication Date: 2015-03-25
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the high toxicity of the current anti-tumor drugs and the poor tolerance of patients, the cure rate of tumor diseases is low. Therefore, it is increasingly urgent to develop anti-tumor drugs with new structures.
Although there are many ways to discover new drugs, the structural modification of existing drugs is still the most successful and economical strategy

Method used

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  • 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings as well as preparation method and application thereof
  • 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings as well as preparation method and application thereof
  • 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings as well as preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0044] The 3,3'-methylene-bisfluoroquinolone derivative containing an ethylquinoline ring in this example is 1-ethyl-6-fluoro-7-piperazin-1-yl-3-[1-ethyl Base-6-fluoro-7-piperazin-1-yl-2,3-dihydro-quinolin-4(1H)-one-3-ylidenemethyl]quinolin-4(1H)-one, its chemical The structural formula is:

[0045]

[0046] That is, R in formula (I) 1 is ethyl, R 2 , R 3 and R 4 are hydrogen atoms, and X is a hydrocarbon group.

[0047] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivatives containing an ethylquinoline ring in this embodiment is: take 0.5g (1.8mmol) of 1-ethyl-6-fluoro-7-piper Azin-1-yl-2,3-dihydro-quinolin-4(1H)-one and 0.55g (1.8mmol) of 1-ethyl-6-fluoro-7-piperazin-1-yl-quinoline -4(1H)-keto-3-carbaldehyde, dissolved in 20ml of absolute ethanol, 0.5ml of piperidine was added dropwise, after reflux reaction for 24h, left overnight, the resulting solid was collected by filtration, and recrystallized with DMF-ethanol to obtain light Yellow cryst...

Embodiment 2

[0049]The 3,3'-methylene-bisfluoroquinolone derivative containing an ethylquinoline ring in this example is 1-ethyl-6-fluoro-7-piperazin-1-yl-3-[1-ethyl Base-6-fluoro-7-(4-methylpiperazin-1-yl)-2,3-dihydro-quinolin-4(1H)-one-3-ylidenemethyl]quinoline-4(1H )-ketone, its chemical structural formula is:

[0050]

[0051] That is, R in formula (I) 1 is ethyl, R 2 is a hydrogen atom, R 3 is methyl, R 4 is a hydrogen atom, and X is a hydrocarbon group.

[0052] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline ring of the present embodiment is: get 0.52g (1.8mmol) of 1-ethyl-6-fluoro-7-( 4-methylpiperazin-1-yl)-2,3-dihydro-quinolin-4(1H)-one with 0.55g (1.8mmol) of 1-ethyl-6-fluoro-7-piperazine- 1-yl-quinolin-4(1H)-one-3-carbaldehyde, dissolved in 20ml of absolute ethanol, added dropwise with 0.5ml of piperidine, after reflux reaction for 24h, the resulting solid was collected by filtration and recrystallized with DMF-ethan...

Embodiment 3

[0054] The 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline ring in this example is 1-ethyl-6-fluoro-7-piperazin-1-yl-3-[1-ring Propan-6-fluoro-7-piperazin-1-yl-2,3-dihydro-quinolin-4(1H)-one-3-ylidenemethyl]quinolin-4(1H)-one, its chemical The structural formula is:

[0055]

[0056] That is, R in formula (I) 1 is cyclopropyl, R 2 , R 3 and R 4 are hydrogen atoms, and X is a hydrocarbon group.

[0057] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivatives containing ethylquinoline ring in this example is: take 0.52g (1.8mmol) of 1-cyclopropyl-6-fluoro-7- Piperazin-1-yl-2,3-dihydro-quinolin-4(1H)-one with 0.55 g (1.8 mmol) of 1-ethyl-6-fluoro-7-piperazin-1-yl-quinone Phenyl-4(1H)-one-3-carbaldehyde was dissolved in 20ml of absolute ethanol, 0.5ml of piperidine was added dropwise, after reflux reaction for 24h, left overnight, the resulting solid was collected by filtration, and recrystallized with DMF-ethanol to obtain Ligh...

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Abstract

The invention discloses a 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings as well as a preparation method and application thereof. The 3,3'-methylene-bisfluoroquinolone derivative containing ethylquinoline rings is a compound having the following structural general formula (I) as shown in the specification, wherein R1 is ethyl, cyclopropyl or fluoroethyl; R2 is H or methyl; R3 is H, methyl or ethyl; R4 is H or methyl; and X is CH, N, F-C or CH3O-C. The preparation method comprises the following steps of effectively combining fluoroquinolone pharmacophores and alpha, beta-unsaturated ketone pharmacophores and constructing two quinolone structural units into the 3,3'-methylene-bisfluoroquinolone derivative by virtue of condensation reaction, the anti-tumor activity is increased, the toxic and side effects to normal cells are decreased, the synergistic and toxicity-reducing effects are achieved and the 3,3'-methylene-bisfluoroquinolone derivative can be used as an anti-tumor active material to develop anticancer drugs having novel structures.

Description

technical field [0001] The invention belongs to the technical field of difluoroquinolone derivative compounds, in particular to a 3,3'-methylene-bisfluoroquinolone derivative containing an ethyl quinoline ring, and also to a 3'-difluoroquinolone derivative containing an ethyl quinoline ring. , Preparation method and application of 3'-methylene-bisfluoroquinolone derivatives. Background technique [0002] Tumor is one of the biggest diseases that threaten human life and health. Due to the high toxicity of the current anti-tumor drugs and the poor tolerance of patients, the cure rate of tumor diseases is low. Therefore, it is increasingly urgent to develop anti-tumor drugs with new structures. Although there are many ways to discover new drugs, the structural modification of existing drugs is still the most successful and economical strategy. Based on the similarity in sequence and function between the target enzyme of antibacterial fluoroquinolones—topoisomerase and the cor...

Claims

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Application Information

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IPC IPC(8): C07D215/38C07D519/00A61P35/00A61P35/02
CPCC07D215/38C07D471/04
Inventor 崔占军文曙光赵辉高留州谢玉锁李涛吴书敏倪礼礼闫强胡国强
Owner HENAN UNIVERSITY
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