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Derivative of 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid as well as preparation method and application of derivative

The technology of fluoronaphthyridone carboxylic acid and isoniazid is applied in the field of preparation of 7-fluoronaphthyridone carboxylic acid derivatives, which can solve the problems of low therapeutic index, phototoxicity, easy generation of drug resistance, etc. Reduce the chance of drug resistance, reduce toxic side effects, and increase the effect of anti-tuberculosis activity

Inactive Publication Date: 2015-04-29
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Isoniazid and fluoroquinolones are the first-line and second-line anti-tuberculosis drugs widely used clinically, but isoniazid has certain liver toxicity, and fluoroquinolones are likely to affect the cartilage development of animals and have phototoxicity. are prone to develop drug resistance, resulting in low therapeutic index

Method used

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  • Derivative of 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid as well as preparation method and application of derivative
  • Derivative of 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid as well as preparation method and application of derivative
  • Derivative of 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid as well as preparation method and application of derivative

Examples

Experimental program
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Embodiment 1

[0049] The 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of this embodiment is 1-cyclopropyl-6-fluoro-7-[3-methyl-4-( Pyridine-4-carbohydrazino)ylidenemethyl-5-piperazin-1-yl-pyrazol-1-yl]-[1,8]naphthyridine-4(1H)-one-3-carboxylic acid, Its chemical structural formula is:

[0050]

[0051] That is, R in formula (I) 1 is a hydrogen atom, R 2 for a hydrogen atom.

[0052] The preparation method of the 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of the present embodiment is as follows: take 1.0 g (2.0 mmol) of 1-cyclopropyl-6-fluoro -7-[3-Methyl-4-(pyridine-4-carbohydrazino)ylidenemethyl-pyrazol-1-yl]-[1,8]naphthyridin-4(1H)-one-3- Carboxylic acid (VI) and 0.34g (4.0mmol) of anhydrous piperazine were added to 20ml of anhydrous acetonitrile for reflux reaction for 12h and left overnight; the resulting solid was collected by filtration and recrystallized ...

Embodiment 2

[0054] The 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of this embodiment is 1-cyclopropyl-6-fluoro-7-[3-methyl-4-( Pyridine-4-carbohydrazino)ylidenemethyl-5-(4-methylpiperazin-1-yl)-pyrazol-1-yl]-[1,8]naphthyridin-4(1H)-one -3-carboxylic acid, its chemical structural formula is:

[0055]

[0056] That is, R in formula (I) 1 is methyl, R 2 for a hydrogen atom.

[0057] The preparation method of the 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of the present embodiment is as follows: take 1.0 g (2.0 mmol) of 1-cyclopropyl-6-fluoro -7-[3-Methyl-5-chloro-4-(pyridine-4-carboxhydrazide)ylidenemethyl-pyrazol-1-yl]-[1,8]naphthyridine-4(1H)- Ketone-3-carboxylic acid (VI) and 0.4g (4.0mmol) of anhydrous methylpiperazine were added to 20ml of anhydrous acetonitrile for reflux reaction for 15h, and left overnight; the resulting solid was collected by filtratio...

Embodiment 3

[0059] The 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of this embodiment is 1-cyclopropyl-6-fluoro-7-[3-methyl-4-( Pyridine-4-carbohydrazino)ylidenemethyl-5-(4-ethylpiperazin-1-yl)-pyrazol-1-yl]-[1,8]naphthyridin-4(1H)-one -3-carboxylic acid, its chemical structural formula is:

[0060]

[0061] That is, R in formula (I) 1 is ethyl, R 2 for a hydrogen atom.

[0062] The preparation method of the 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative of the present embodiment is as follows: take 1.0 g (2.0 mmol) of 1-cyclopropyl-6-fluoro -7-[3-Methyl-5-chloro-4-(pyridine-4-carboxhydrazide)ylidenemethyl-pyrazol-1-yl]-[1,8]naphthyridine-4(1H)- Ketone-3-carboxylic acid (VI) and 0.46g (4.0mmol) of anhydrous ethylpiperazine were added to 20ml of anhydrous acetonitrile for reflux reaction for 24h, and left overnight; the resulting solid was collected by filtration ...

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Abstract

The invention discloses a derivative of 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid as well as a preparation method and an application of the derivative. The derivative of the 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid is a compound having a structural general formula (I), wherein R1 is H, methyl or ethyl; R2 is H or methyl. According to the derivative of the 7-(piperazine substituted pyrazole aldehyde isoniazid hydrazone) fluoronaphthyridinone carboxylic acid, fluoroquinolone, isoniazid and pyrazole aldehyde hydrazine are effectively combined to form a compound having a new structure, the joint of pharmacophores and the mutual complementation of structures are realized and the overlapping and cooperation of the activity are achieved; the antituberculous activity is added, the toxic and side effects of fluoroquinolone and isoniazid on normal cells are reduced, and meanwhile, the probability of drug resistance of mycobacterium tuberculosis to the drug is also reduced; as a result, the derivative can be used as an antituberculous active substance to develop antituberculous drug having a brand new structure.

Description

technical field [0001] The invention belongs to the technical field of flunalidone carboxylic acid derivatives, and specifically relates to a 7-(piperazine-substituted pyrazole aldehyde isoniazid hydrazone) flunalidinone carboxylic acid derivative, and also relates to a 7- (Piperazine substituted pyrazole aldehyde isoniazid hydrazone) flunalidone carboxylic acid derivatives preparation method and application. Background technique [0002] Mycobacterium tuberculosis infection is a major disease that threatens global public health security, especially the emergence of drug resistance of Mycobacterium tuberculosis, which has caused great harm to public health. Therefore, people look forward to the development of new anti-tuberculosis drugs as soon as possible to overcome the current increasingly serious tuberculosis resistance problem. However, due to the difficulty of innovating an anti-tuberculosis drug with a new chemical structure, no new chemical entity drug has been born...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04A61K31/496A61P31/06
CPCC07D471/04
Inventor 杜耀武王军王蕊高留州谢玉锁闫强吴书敏倪礼礼胡国强
Owner HENAN UNIVERSITY
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