Ciprofloxacin C3 amide derivative, preparation method thereof and application

A technology of amide derivatives and ciprofloxacin, which is applied in the field of medicine, can solve the problems of ciprofloxacin C3 amide derivatives that have not yet had sonodynamic activity, and achieve high antibacterial activity, easy post-processing, and good sonodynamic activity Effect

Active Publication Date: 2017-02-22
LIAONING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no research report on ciproflo...

Method used

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  • Ciprofloxacin C3 amide derivative, preparation method thereof and application
  • Ciprofloxacin C3 amide derivative, preparation method thereof and application
  • Ciprofloxacin C3 amide derivative, preparation method thereof and application

Examples

Experimental program
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Embodiment 1

[0019] (1) 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-(4-ethoxycarbonyl)piperazinyl]quinoline-3 provided in this example -(N-p-tolyl) formamide, its structural formula is as follows:

[0020]

[0021] (2) Preparation method

[0022] Weigh 3.8582g of ciprofloxacin hydrochloride into a round bottom flask, add 50mL of anhydrous sodium sulfate dried dichloromethane, heat and stir at 38°C, gradually add 20mmol of anhydrous sodium sulfate dried triethylamine dropwise To the reaction solution, adjust the pH of the reaction solution to 7.5-8.5. Then, within half an hour, 15 mmol of ethyl chloroformate was slowly added dropwise to the reaction liquid, and stirred under reflux at 20° C. until the reaction liquid became clear. Add an appropriate amount of triethylamine dropwise to the reaction solution to make the pH 7.5-8.5, then add 10 mmol of p-aminotoluene, and continue to reflux for half an hour. After the reaction solution was cooled, it was distilled under reduced pressur...

Embodiment 2

[0027] (1) 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-(4-ethoxycarbonyl)piperazinyl]quinoline-3 provided in this example -(N-p-chlorophenyl) formamide, its structural formula is:

[0028]

[0029] (2) Preparation method

[0030] Weigh 3.8582g of ciprofloxacin hydrochloride into a round bottom flask, add 50mL of anhydrous sodium sulfate dried dichloromethane, heat and stir at 38°C, gradually add 20mmol of anhydrous sodium sulfate dried triethylamine dropwise To the reaction solution, adjust the pH of the reaction solution to 7.5-8.5. Then, within half an hour, 15 mmol of ethyl chloroformate was slowly added dropwise to the reaction liquid, and stirred under reflux at 20° C. until the reaction liquid became clear. Add an appropriate amount of triethylamine dropwise to the reaction solution to make the pH 7.5-8.5, then add 10 mmol of p-aminochlorobenzene, and continue to reflux for half an hour. After the reaction liquid was cooled, the liquid was distilled under reduced...

Embodiment 3

[0035] (1) 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[1-(4-ethoxycarbonyl)piperazinyl]quinoline-3 provided in this example -(N-methoxyphenyl) formamide, its structural formula is:

[0036]

[0037] (2) Preparation method

[0038] Weigh 3.8582g of ciprofloxacin hydrochloride into a round bottom flask, add 50mL of anhydrous sodium sulfate dried dichloromethane, heat and stir at 38°C, gradually add 20mmol of anhydrous sodium sulfate dried triethylamine dropwise To the reaction solution, adjust the pH of the reaction solution to 7.5-8.5. Then, within half an hour, 15 mmol of ethyl chloroformate was slowly added dropwise to the reaction liquid, and stirred under reflux at 20° C. until the reaction liquid became clear. Add an appropriate amount of triethylamine dropwise to the reaction solution to make the pH 7.5-8.5, then add 10 mmol of m-methoxyaniline, and continue to reflux for half an hour. After the reaction liquid was cooled, the liquid was distilled under reduced pres...

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Abstract

The invention discloses a ciprofloxacin C3 amide derivative, a preparation method thereof and an application. The ciprofloxacin C3 amide derivative is provided with a structure as shown in a formula (I). Ciprofloxacin hydrochloride is added into excessive methylene dichloride, triethylamine is dripped to adjust the pH (potential of hydrogen) of reaction liquid to be 7.5-8.5, an appropriate amount of ethyl chloroformate is added, the reaction liquid is subjected to return flow agitation at the temperature of 20 DEG C and is clear, triethylamine is dripped into the reaction liquid so that the pH of the reaction liquid is 7.5-8.5, arylamine is added, return flow is continued for 1-2 hours, and the reaction liquid is cooled, reduced pressure distillation and concentration to obtain a target product. The ciprofloxacin C3 amide derivative has good sonodynamic activity and is obviously superior to ciprofloxacin in terms of microwave synergistic antibacterial effect.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a ciprofloxacin C3 amide derivative, a preparation method thereof and an application in the medicine field. Background technique [0002] Sonodynamic therapy is a new method of treating tumors by utilizing the strong penetrating power of ultrasound combined with sonosensitizers. Ultrasonic waves penetrate tissue to excite the sonosensitizers accumulated in tumor tissues, generating reactive oxygen species with strong oxidative activity, such as singlet Oxygen, free radicals, etc., oxidize and destroy the substrates of tumor cell proliferation, leading to tumor cell death. In recent years, research results have found that ciprofloxacin not only exhibits certain anti-tumor activity, but also has certain sonosensitivity. Certain structural modifications to ciprofloxacin may have better anti-tumor effects and have clinical application prospects. sound sensitizer. At pr...

Claims

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Application Information

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IPC IPC(8): C07D215/56A61K31/496A61K41/00A61P35/00A61P31/04
CPCA61K31/496A61K41/0033C07D215/56
Inventor 刘彬董博阳刘冰弥王新景姣姣刘昌志
Owner LIAONING UNIVERSITY
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