N-(4-methylphenyl)-2,2,2-trifluoroacetimidoylciprofloxacin | 1301158-66-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(4-methylphenyl)-2,2,2-trifluoroacetimidoylciprofloxacin
• 英文别名: 1-cyclopropyl-6-fluoro-7-[4-[N-(4-methylphenyl)-C-(trifluoromethyl)carbonimidoyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 1301158-66-6
• 化学式: C₂₆H₂₄F₄N₄O₃
• 分子量: 516.495
• InChiKey: HYSTVRSDJSEPQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  76.4
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 在 四氯化碳 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-methylphenyl)-2,2,2-trifluoroacetimidoylciprofloxacin
  参考文献：
  名称：

  N-芳基-2,2,2-三氟乙酰亚胺基哌嗪基喹诺酮衍生物的合成及其抗菌性能

  摘要：

  N-取代的三氟乙酰亚胺基氯用于合成新的哌嗪基喹诺酮衍生物。这些反应以良好的收率提供了N-芳基-2，2，2-三氟乙酰亚胺基哌嗪基喹诺酮衍生物。评价了两种选择的化合物的抗菌活性。这些化合物显示出良好的抗菌活性。

  DOI：

  10.1016/j.jfluchem.2011.02.002

文献信息

• An Investigation into Antibacterial Activity of Fluoroquinolone-Derived Compounds on Two Gram-Negative Bacteria; Escherichia coli and Pseudomonas aeruginosa
  作者：Shokrollah Assar、Ali Darehkordi、Mohammad Moradi、Mahmood Sheikh Fathollahi、Soudeh Khanamani Falahati-Pour、Gholamhossein Hassanshahi

  DOI：10.7860/jcdr/2019/41883.13117

  日期：——

  Introduction: Quinolones are known as a class of antibiotics inhibiting two central enzymes involved in DNA replication and transcription i.e., DNA gyrase and topoisomerase IV. Among them, fluoroquinolones can be developed via substituting fluorine atoms at the sixth position of core quinolone structure, thereby enhancing antibacterial activity. As a result, growth and proliferation of bacteria may be prevented through new compounds derived from fluoroquinolones and somehow may strengthen their antibacterial effects.Aim: To assess the probable antibacterial activity of two fluoroquinolone derivatives on Pseudomonas aeruginosa and Escherichia coli as two gram-negative resistant bacteria.Materials and Methods: The present study was designed and conducted to measure inhibitory concentrations of N-4-methyl (phenyl)-2,2,2-trifluoroacetimidoyl ciprofloxacin (5a) and N-4-methyl (phenyl)-2,2,2-trifluoroacetimidoyl norfloxacin (5b) as two synthetic derivatives of fluoroquinolones. In addition, real-time PCR (RT-PCR) technique was used to assay the performance of these two derivatives on DNA gyrase gene expression levels in Escherichia coli (E. coli) and Pseudomonas aeruginosa (P. aeruginosa) as gram-negative bacteria. Broth microdilution method and disc diffusion test were also employed to determine the Minimum Inhibitory Concentration (MIC) of these synthetic compounds in comparison with conventional antibiotics of gentamycin and ciprofloxacin (a fluoroquinolone). The p< 0.05 was assumed as statistically significant.Results: According to the findings; Zone Of Inhibition (ZOI) of 5a in P. aeruginosa and E. coli (18.5 +/- 0.1 and 13.2 +/- 0.1 mm respectively) compared with ZOI of ciprofloxacin (28.0 +/- 2.0 mm and 18.3.+/- 0.1 mm) and gentamycin (21 +/- 0.1 mm and 19.0 +/- 0.1 mm). There was no significant difference between the antibacterial effect of 5a and tested antibiotics (p>0.05). So, their antibacterial effects were assumed to be less than the given antibiotics. In contrast, 5b generated a diameter of ZOI in P. aeruginosa and E. coli (28 +/- 0.1 and 38 +/- 0.1 mm) in comparison with ciprofloxacin (28.0 +/- 0.1 and 17.9 +/- 0.1 mm) and gentamycin (21 +/- 0.1 mm and 19.0 +/- 0.1 mm) showed a statistically significant difference (p<0.001). The results of the broth microdilution method also confirmed findings from the disc diffusion test. On the other hand, 5b brought about a significant reduction of DNA gyrase expression levels in both bacteria, while 5a did not show such a significant effect in this domain.Conclusion: The results of this study suggested that 5b could be used as a new and alternative antibiotic for gentamycin or ciprofloxacin against infections caused by E. coli and P. aeruginosa. However, further research focused on various dimensions, including corresponding complications, as well as clinical trials are required to draw a definite conclusion on these synthetic compounds.
• Synthesis of N-aryl-2,2,2-trifluoroacetimidoyl piperazinylquinolone derivatives and their antibacterial evaluations
  作者：Ali Darehkordi、Mahmood Javanmiri、Somayeh Ghazi、Shokrollah Assar

  DOI：10.1016/j.jfluchem.2011.02.002

  日期：2011.4

  N-substituted trifluoroacetimidoyl chlorides were used for the synthesis of new piperazinylquinolone derivatives. These reactions provided N-aryl-2,2,2-trifluoroacetimidoyl piperazinylquinolone derivatives in good yields. Two selected compounds were evaluated for their antibacterial activities. These compounds displayed good antibacterial activities.

  N-取代的三氟乙酰亚胺基氯用于合成新的哌嗪基喹诺酮衍生物。这些反应以良好的收率提供了N-芳基-2，2，2-三氟乙酰亚胺基哌嗪基喹诺酮衍生物。评价了两种选择的化合物的抗菌活性。这些化合物显示出良好的抗菌活性。