Acrylketone derivative of N-methyl gatifloxacin and preparation method and application of acrylketone derivative
A technology of gatifloxacin and acrylone, which is applied to the acrylone derivative of N-methyl gatifloxacin and its preparation field, can solve the problems such as the uncertainty of the effect of the C-3 carboxyl group of fluoroquinolone, and achieve an increase in anti-tumor effect. Activity and anti-drug resistance, the effect of reducing side effects
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Embodiment 1
[0031] 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-3-cinnamoyl-8-methoxy-quinoline-4(1 H )-ketone (I-1), its chemical structural formula is:
[0032]
[0033] That is, Ar in formula I is phenyl.
[0034] The preparation method of this compound is:
[0035] (1) Using N-methylgatifloxacin shown in Formula II as a raw material, react with carbonyldiimidazole (CDI) to prepare N-methylgatifloxacin imidazole amide compound shown in Formula III, and its specific preparation Methods as below:
[0036]
[0037] Take 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-8-methoxy-quinoline-4(1 H 20 g (51.0 mmol) of )-keto-3-carboxylic acid II was dissolved in 500 mL of anhydrous acetonitrile, 15.2 g (94.0 mmol) of carbonyldiimidazole was added, and the mixed reaction was stirred and refluxed in a water bath until the raw material II disappeared. Leave it at room temperature, collect the resulting solid by filtration, and recrystallize with acetone to obtain the light...
Embodiment 2
[0046] 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-3-(4-methoxycinnamoyl)-8-methoxy-quinoline-4 (1 H )-ketone (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:
[0050] (1) 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-8-methoxy-quinoline-4(1 H )-ketone-3-ethanone V is prepared with reference to steps (1)-(3) of Implementation 1, the solvent in step (1) is replaced by tetrahydrofuran, the mixture of N-methylgatifloxacin and carbonyldiimidazole The molar ratio is 1:1.0;
[0051] (2) Take 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-8-methoxy-quinoline-4(1 H 1.2 g (3.0 mmol) of )-keto-3-ethanone V was dissolved in 20 mL of absolute ethanol, and 0.57 g (4.2 mmol) of 4-methoxybenzaldehyde and base catalyst piperidine (0.1 mL) were added. The mixed reactants were refluxed for 20 h, left at room temperature, and the resulting solid was coll...
Embodiment 3
[0053] 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-3-(3,4-dioxymethylenecinnamoyl)-8-methoxy- Quinoline-4(1 H )-ketone (I-3), its chemical structural formula is:
[0054]
[0055] That is, Ar in formula I is 3,4-(dioxymethylene)phenyl.
[0056] The preparation method of this compound is:
[0057] (1) 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-8-methoxy-quinoline-4(1 H )-keto-3-ethanone V is prepared with reference to steps (1)-(3) of Implementation 1, and the solvent in step (1) is replaced by dioxane, N-methylgatifloxacin and carbonyl The mol ratio of diimidazole is 1:2.0;
[0058] (2) Take 1-cyclopropyl-6-fluoro-7-(3,4-dimethylpiperazin-1-yl)-8-methoxy-quinoline-4(1 H )-keto-3-ethanone V1.2 g (3.0 mmol) was dissolved in 20 mL of absolute ethanol, 0.53 g (3.5 mmol) of 3,4-dioxymethylene benzaldehyde and base catalyst piperidine (0.1 mL). The mixed reactants were refluxed for 20 h, left at room temperature, and the resulting solid was collected b...
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