3,3'-methylene-bisfluoroquinolone derivative containing cyclopropylquinoline ring as well as preparation method and application of 3,3'-methylene-bisfluoroquinolone derivative

A technology of cyclopropaquinoline ring and difluoroquinolone, which is applied in the field of difluoroquinolone derivative compounds, can solve the problems of high toxicity of antitumor drugs, poor patient tolerance, low cure rate of tumor diseases, etc., and achieves increased antitumor activity, The effect of reducing toxic side effects

Inactive Publication Date: 2015-02-25
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 drug

Method used

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  • 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropylquinoline ring as well as preparation method and application of 3,3'-methylene-bisfluoroquinolone derivative
  • 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropylquinoline ring as well as preparation method and application of 3,3'-methylene-bisfluoroquinolone derivative
  • 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropylquinoline ring as well as preparation method and application of 3,3'-methylene-bisfluoroquinolone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this embodiment is 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-3-[1- Ethyl-6-fluoro-7-piperazin-1-yl-2,3-dihydro-quinolin-4(1H)-one-3-ylidenemethyl]quinolin-4(1H)-one, which The chemical structural formula is:

[0044]

[0045] That is, R in the formula (I) is a hydrogen atom, and R 1 is ethyl, R 2 and R 3 are hydrogen atoms, and X is a hydrocarbon group.

[0046] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this example is as follows: take 0.50 g (1.6 mmol) of 1-cyclopropyl-6-fluoro-7- Piperazin-1-yl-quinolin-4(1H)-one-3-carbaldehyde and 0.44g (1.6mmol) of 1-ethyl-6-fluoro-7-piperazin-1-yl-2,3- Dihydro-quinolin-4(1H)-one was dissolved in 20ml of absolute ethanol, 0.2ml of piperidine was added dropwise, and after reflux reaction for 24h, it was allowed to stand overnight, and the resulting solid was collected by...

Embodiment 2

[0048] The 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this embodiment is 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-3-[1- Ethyl-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:

[0049]

[0050] That is, R in formula I is a hydrogen atom, R 1 is ethyl, R 2 is methyl, R 3 is a hydrogen atom, and X is a hydrocarbon group.

[0051] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this example is as follows: take 0.50 g (1.6 mmol) of 1-cyclopropyl-6-fluoro-7- Piperazin-1-yl-quinolin-4(1H)-one-3-carbaldehyde and 0.47g (1.6mmol) of 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl )-2,3-dihydro-quinolin-4(1H)-one, dissolved in 20ml of absolute ethanol, added dropwise 0.2ml of piperidine, after reflux for 24h, left overnight, filtered the resulting solid, and washed with DMF - Recrystall...

Embodiment 3

[0053] The 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this embodiment is 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-3-[1- Cyclopropyl-6-fluoro-7-piperazin-1-yl-2,3-dihydro-quinolin-4(1H)-one-3-ylidenemethyl]quinolin-4(1H)-one, Its chemical structural formula is:

[0054]

[0055] That is, R in formula I is a hydrogen atom, R 1 is cyclopropyl, R 2 and R 3 is a hydrogen atom, and X is a hydrocarbon group.

[0056] The preparation method of the 3,3'-methylene-bisfluoroquinolone derivative containing cyclopropaquinoline ring in this embodiment is as follows: take 0.50g (1.6mmol) 1-cyclopropyl-6-fluoro-7-piper Azin-1-yl-quinolin-4(1H)-one-3-carbaldehyde and 0.46g (1.6mmol) of 1-cyclopropyl-6-fluoro-7-piperazin-1-yl-2,3- Dihydro-quinolin-4(1H)-one was dissolved in 20ml of absolute ethanol, 0.2ml of piperidine was added dropwise, and after reflux reaction for 24h, it was allowed to stand overnight, and the resulting solid was collected by...

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Abstract

The invention discloses a 3,3'-methylene-bisfluoroquinolone derivative containing a cyclopropylquinoline ring as well as a preparation method and application of the 3,3'-methylene-bisfluoroquinolone derivative. The 3,3'-methylene-bisfluoroquinolone derivative containing the cyclopropylquinoline ring is a compound having a structural general formula as shown in the specification, wherein R is H, methyl or ethyl; R1 is ethyl, cyclopropyl or fluoroethyl; R2 is H, methyl or ethyl; R3 is H or methyl; and X is CH, N, F-C or CH3O-C. According to the 3,3'-methylene-bisfluoroquinolone derivative containing the cyclopropylquinoline ring, based on the combination principle of pharmacophores, the superposition of bisfluoroquinolone pharmacophore and alpha, beta-unsaturated ketone is achieved, and a 'fluoroquinolone chalcone' derivative is designed and synthesized; by the structural complementation, the anti-tumor activity is increased, the toxic or side effect on normal cells is decreased so as to achieve synergistic and toxicity-attenuation effects and the 3,3'-methylene-bisfluoroquinolone derivative can be used as an anti-tumor active substance to develop an anti-tumor drug having a new structure.

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 a cyproquinoline ring, and at the same time relates to a 3, 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 for new drug development. Based on the similarity in sequence and function between the target enzyme of antibacterial fluoroquinolones—topoisomerase and the corresponding topoisomerase...

Claims

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Application Information

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IPC IPC(8): C07D215/38C07D471/04A61P35/00A61P35/02
CPCC07D215/38C07D471/04
Inventor 刘洋丁勇赵辉王蕊高留州李涛谢玉锁闫强吴书敏倪礼礼胡国强
Owner HENAN UNIVERSITY
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