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
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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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