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Fluoroquinolone acetal isoniazone, and preparation method and application thereof

A technology of fluoroquinolone aldehyde and quinolone aldehyde, which is applied in the field of fluoroquinolone derivative compounds, can solve problems such as phototoxicity, poor efficacy of tuberculosis, and affect animal cartilage development, and achieve the effects of reducing toxic side effects and drug resistance.

Inactive Publication Date: 2012-12-19
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, because fluoroquinolones (FQs) affect cartilage development in animals, have phototoxicity, and are less effective against tuberculosis than classic first-line anti-tuberculosis drugs such as isoniazid (INH) and rifampicin (RFP), so this class Drugs have certain defects in the treatment of tuberculosis
However, isoniazid is an anti-tuberculosis drug that has a strong killing effect on Mycobacterium tuberculosis, but it has certain liver toxicity.

Method used

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  • Fluoroquinolone acetal isoniazone, and preparation method and application thereof
  • Fluoroquinolone acetal isoniazone, and preparation method and application thereof
  • Fluoroquinolone acetal isoniazone, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The fluoroquinolone aldehyde isonicotinoid hydrazone in this example is (S)-N'-[6-fluoro-7-(4-methylpiperazin-1-yl)-1,8-(2,1-oxopropane Base)-quinoline (1H)-4-one-3-methylene]isoniazone, its chemical structural formula is:

[0033]

[0034] That is, R in formula I 1 for methyl(S), R 2 is a hydrogen atom, R 3 is methyl, R 4 is a hydrogen atom, and X is an oxygen atom.

[0035] The preparation method of the fluoroquinolone aldehyde isonicotinoid hydrazone of the present embodiment is: take (S)-6-fluoro-1,8-(2,1-oxopropyl)-7-(4-methylpiperazine-1 -yl)-3-formyl-4(1H)-quinolinone 0.35g (1mmol), absolute ethanol 12ml, heated to dissolve, then add isoniazid 0.14g (1mmol), reflux for 3h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.37 g of the fluoroquinolone aldehyde isonicotinoid hydrazone compound of Example 1, with a yield of 81%, m.p.211.9-214.3°C. 1 HNMR (DMSO-d 6 , 400MHz) δ: 11.9...

Embodiment 2

[0037] The fluoroquinolone aldehyde isonicotinoid hydrazone in this embodiment is N'-[6-fluoro-7-(4-methylpiperazin-1 base)-1,8-(2,1-oxopropyl)-quinoline (1H)-4-keto-3-methylene]isonicotinamide, its chemical structural formula is:

[0038]

[0039] That is, R in formula I 1 is methyl, R 2 is a hydrogen atom, R 3 is methyl, R 4 is a hydrogen atom, and X is an oxygen atom.

[0040] The preparation method of the fluoroquinolone aldehyde isonicotinoid hydrazone of the present embodiment is: take 6-fluoro-1,8-(2,1-oxypropyl)-7-(4-methylpiperazin-1-yl)- 0.35g (1mmol) of 3-formyl-4(1H)-quinolinone and 15ml of absolute ethanol were heated until dissolved, then 0.14g (1mmol) of isoniazid was added, and refluxed for 3h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.38 g of the fluoroquinolone aldehyde isonicotinoid hydrazone compound of Example 2, with a yield of 83%, m.p.293.5-295.6°C. 1 HNMR (DMS...

Embodiment 3

[0042] The fluoroquinolone aldehyde isonicotinoid hydrazone of the present embodiment is (S)-N'-[6-fluoro-7-piperazin-1-yl-1,8-(2,1-oxopropyl)-quinoline ( 1H)-4-keto-3-methylene]isoniazone, its chemical structural formula is:

[0043]

[0044] That is, R in formula I 1for methyl(S), R 2 is a hydrogen atom, R 3 is a hydrogen atom, R 4 is a hydrogen atom, and X is an oxygen atom.

[0045] The preparation method of the fluoroquinolone aldehyde isonicotinoid hydrazone of the present embodiment is: take (S)-6-fluoro-1,8-(2-methylethyleneoxy)-7-(piperazin-1-yl) - 0.33g (1mmol) of 3-formyl-4(1H)-quinolinone, 12ml of absolute ethanol, heated until dissolved, then added 0.14g (1mmol) of isoniazid, and heated to reflux for 3h. After standing overnight, the resulting solid was collected by filtration, washed with absolute ethanol, and dried to obtain 0.34 g of the fluoroquinolone aldehyde isonicotinoid hydrazone compound of Example 3, with a yield of 76% and m.p.>300°C. 1 HNMR (...

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Abstract

The invention discloses a fluoroquinolone acetal isoniazone, of which the chemical structure general formula is disclosed as Formula I shown in the description, wherein R1 is hydrogen atom or methyl group; R2 is hydrogen atom or amino group; R3 is hydrogen atom, methyl group, ethyl group, formacyl group, acetyl group, aroyl group or sulfonyl group; R4 is hydrogen atom or methyl group; and X is oxygen atom or sulfur atom. The fluoroquinolone isoniazone disclosed by the invention implements complementarity between the two anti-tuberculosis medicines fluoroquinolone and the isoniazide, lowers the toxic and side effect of the fluoroquinolone and the isoniazide, reduces the generation probability of drug resistance of Mycobacterium tuberculosis for the double-effect antimicrobial agent, and can be used as an anti-Mycobacterium tuberculosis medicine for brand-new structure development of medicinal active substances.

Description

technical field [0001] The invention relates to a fluoroquinolone derivative compound, in particular to a fluoroquinolone aldehyde isonicotidine hydrazone, a preparation method of the fluoroquinolone aldehyde isonicotidine hydrazone, and its application in anti-tuberculosis drugs. Background technique [0002] Tuberculosis is a major threat to human health. At present, more than 10 million people in the world have been infected with tuberculosis, and about 1.5 million people have died of tuberculosis infection. Currently, tuberculosis is the infectious disease with the highest mortality rate except AIDS. Due to the long clinical development process of anti-tuberculosis drugs, it is difficult to find active new compounds and develop them into clinically promising anti-tuberculosis drugs. In the 40 years since the advent of rifampicin, no new compound has been used for anti-tuberculosis treatment. In addition, irrational drug use and incomplete treatment make the infection ra...

Claims

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Application Information

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IPC IPC(8): C07D498/06C07D513/06A61K31/5383A61K31/542A61P31/06
Inventor 胡国强王国强敬永升
Owner HENAN UNIVERSITY
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