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Levofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof

A technology of levofloxacin and amide derivatives, applied in the field of innovative drug synthesis

Inactive Publication Date: 2015-08-19
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the molecular structure construction between the fluoroquinolone skeleton and the rhodanine skeleton has not been reported yet.

Method used

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  • Levofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof
  • Levofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof
  • Levofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Levofloxacin (2-thio-5-benzoylidene-thiazolidin-4-one-3-yl)-amide (I-1), its chemical structural formula is:

[0042]

[0043] That is, Ar in formula I is phenyl.

[0044] The preparation method of this compound is: get levofloxacin (rhodanine-3-base)-amide (IV) 1.0g (2.0mmol) and anhydrous sodium acetate 0.20g (2.4mmol) and dissolve in 15mL glacial acetic acid, add benzaldehyde 0.25g (2.4mmol), the mixed reactant was refluxed for 12h. The solvent was distilled off under reduced pressure, the residue was dissolved in water (20 mL), and 0.1 g of activated carbon was added to decolorize at 60° C. for 0.5 h, and filtered. The filtrate was basified to pH 9.0 with concentrated aqueous ammonia, extracted with chloroform (3×15 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was recovered under reduced pressure to dryness, and recrystallized from ethanol-DMF (V:V=5:1) to obtain a light yellow crystal (I-1), with a yield of 67.5%, ...

Embodiment 2

[0046] Levofloxacin (2-thio-5-p-methoxybenzylidene-thiazolidin-4-one-3-yl)-amide (I-2), its chemical structural formula is:

[0047]

[0048] That is, Ar in formula I is p-methoxyphenyl.

[0049] The preparation method of this compound is: take levofloxacin (rhodanine-3-yl)-amide (IV) 1.0g (2.0mmol) and anhydrous sodium acetate 0.20g (2.4mmol) and dissolve in 15mL glacial acetic acid, add p-formazine Oxybenzaldehyde 0.30g (2.2mmol), the mixed reactants were refluxed for 12h. The solvent was distilled off under reduced pressure, the residue was dissolved in water (20 mL), and 0.1 g of activated carbon was added to decolorize at 60° C. for 0.5 h, and filtered. The filtrate was basified to pH 9.0 with concentrated aqueous ammonia, extracted with chloroform (3×15 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was recovered under reduced pressure to dryness, and recrystallized from ethanol-DMF (V:V=5:1) to obtain a light yellow cryst...

Embodiment 3

[0051] Levofloxacin (2-thio-5-o-methoxybenzylidene-thiazolidin-4-one-3-yl)amide (I-3), its chemical structural formula is:

[0052]

[0053] That is, Ar in formula I is o-methoxyphenyl.

[0054] The preparation method of this compound is: take levofloxacin (rhodanine-3-yl)-amide (IV) 1.0g (2.0mmol) and anhydrous sodium acetate 0.20g (2.4mmol) and dissolve in 15mL glacial acetic acid, add o-formazan Oxybenzaldehyde 0.30g (2.2mmol), the mixed reactants were refluxed for 12h. The solvent was distilled off under reduced pressure, the residue was dissolved in water (20 mL), and 0.1 g of activated carbon was added to decolorize at 60° C. for 0.5 h, and filtered. The filtrate was basified to pH 9.0 with concentrated aqueous ammonia, extracted with chloroform (3×15 mL), and the combined organic phases were dried over anhydrous sodium sulfate. The solvent was recovered under reduced pressure to dryness, and recrystallized from ethanol-DMF (V:V=5:1) to obtain a light yellow crystal...

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Abstract

The invention discloses a levofloxacin (rhodanine unsaturated ketone) amide derivative and a preparation method and an application thereof. The levofloxacin (rhodanine unsaturated ketone) amide derivative adopts the following chemical structural general formula I (shown in the specification); and in the formula I, Ar represents a benzene ring or a substituted benzene ring or a furan ring or a pyridine ring. On the basis of a medicine molecule construction strategy of pharmacophore splice, the levofloxacin (rhodanine unsaturated ketone) amide derivative disclosed by the invention implements superposition of four pharmacophores of a chiral tricyclic fluoroquinolone skeleton, amide, rhodanine and alpha, beta-unsaturated ketone, so that the antineoplastic activity of a new compound is improved, the toxic or side effects on normal cells are reduced, and the levofloxacin (rhodanine unsaturated ketone) amide derivative can be used as an antineoplastic active substance for developing an antineoplastic medicament of a brand-new structure.

Description

technical field [0001] The invention belongs to the technical field of innovative drug synthesis, and specifically relates to a levofloxacin (rhodanine unsaturated ketone) amide derivative, and also relates to a levofloxacin (rhodanine unsaturated ketone) amide derivative preparation method and its Application in antitumor drugs. Background technique [0002] New drug innovation originates from the discovery of lead substances, and rational drug design based on structure or mechanism is an effective method to discover lead substances. Antibacterial fluoroquinolones are based on 1-substituted-6-fluoro-quinoline (naphthyridine)-4-one-3-carboxylic acid as the dominant skeleton, and its target is topoisomerase (Topo). Functionally, it is similar to the corresponding Topo in mammalian cells, and this enzyme is also an important target of anti-tumor drugs. Therefore, structural modification of existing fluoroquinolone drugs can convert their antibacterial activity into antitumor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06A61P35/00A61P35/02
CPCC07D498/06
Inventor 刘彬贾彩云王蕊闫强吴书敏倪礼礼胡国强
Owner HENAN UNIVERSITY
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