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N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof

A technology of methyl ciprofloxacin and rhodanine, applied in the directions of drug combination, organic chemistry, anti-tumor drugs, etc.

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 unsaturated ketoamide structure constructed by splicing fluoroquinolone skeleton and rhodanine skeleton has not been reported yet.

Method used

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  • N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof
  • N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof
  • N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2-thio-5-benzyl Forkyl-thiazolidin-4-one-3-yl)-amide (I-1), its chemical structural formula is:

[0044]

[0045] That is, Ar in formula I is phenyl.

[0046] The preparation method of this compound is: take 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2 -thio-thiazolidin-4-one-3-yl)-amide (V) 1.0g (2.1mmol) and anhydrous sodium acetate 0.21g (2.5mmol) were dissolved in 15mL of glacial acetic acid, added benzaldehyde 0.27g ( 2.5mmol), 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 sul...

Embodiment 2

[0048] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2-thio-5-p-methyl Oxybenzylidene-thiazolidin-4-one-3-yl)-amide (I-2), its chemical structural formula is:

[0049]

[0050] That is, Ar in formula I is p-methoxyphenyl.

[0051] The preparation method of this compound is: take 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2 -Thio-thiazolidin-4-one-3-yl)-amide (V) 1.0g (2.1mmol) and anhydrous sodium acetate 0.21g (2.5mmol) were dissolved in 15mL of glacial acetic acid, and p-methoxybenzene was added 0.34g (2.5mmol) of formaldehyde, and 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 o...

Embodiment 3

[0053] 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2-thio-5-o-methyl Oxybenzylidene-thiazolidin-4-one-3-yl)amide (I-3), its chemical structural formula is:

[0054]

[0055] That is, Ar in formula I is o-methoxyphenyl.

[0056] The preparation method of this compound is: take 1-cyclopropyl-6-fluoro-7-(4-methyl-piperazin-1-yl)-quinolin-4(1H)-one-3-carboxylic acid (2 -Thio-thiazolidin-4-one-3-yl)-amide (V) 1.0g (2.1mmol) and anhydrous sodium acetate 0.21g (2.5mmol) were dissolved in 15mL of glacial acetic acid, and p-methoxybenzene was added 0.34g (2.5mmol) of formaldehyde, and the mixed reactants were refluxed for 12h. The solvent was evaporated under reduced pressure, and the residue was dissolved in water (20 mL), added with 0.1 g of activated carbon for decolorization 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 o...

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Abstract

The invention discloses an N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative and a preparation method and an application thereof. The N-methyl ciprofloxacin (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. The N-methyl ciprofloxacin (rhodanine unsaturated ketone) amide derivative disclosed by the invention implements superposition of three pharmacophores of a chiral tricyclic fluoroquinolone skeleton, amide and rhodanine alpha, beta-unsaturated ketone, so that the antineoplastic activity of a new compound is improved, and the toxic or side effects on normal cells are reduced, and the N-methyl ciprofloxacin (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 kind of N-methylciprofloxacin (rhodanine unsaturated ketone) amide derivative, and also relates to N-methylciprofloxacin (rhodanine not saturated ketone) A preparation method of saturated ketone) amide derivatives and its application in the preparation of antitumor drugs. Background technique [0002] New drug innovation originates from the discovery of lead substances, and structure-based rational drug design is an effective method to discover lead substances. Among the various pharmacophore structures, five-membered heterocyclic ketones with a wide range of pharmacological activities, especially rhodanine, have become the dominant framework in medicinal chemistry and are widely used in the construction of new drug molecular chemical frameworks. It mainly includes α, β-unsaturated ketone derivatives constructed by the condensation reaction of acti...

Claims

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Application Information

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IPC IPC(8): C07D417/12C07D417/14A61P35/00A61P35/02
CPCC07D417/12C07D417/14
Inventor 刘英杰王蕊闫强吴书敏倪礼礼胡国强
Owner HENAN UNIVERSITY
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