7-(4-benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1198425-72-7

• 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: 7-(4-benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 7-(4-Benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 1198425-72-7
• 化学式: C₂₆H₂₆FN₃O₅
• 分子量: 479.508
• InChiKey: GZDUOMPACGUQFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  35
• 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：
  90.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯甲酰氯 、 加替沙星 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到7-(4-benzoyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis, characterization, antibacterial, antifungal, and immunomodulating activities of gatifloxacin derivatives

  摘要：

  Gatifloxacin is a synthetic broad-spectrum fluorquinolone antibacterial agent with a 3-methylpiperazinyl-side chain at position 7 and a methoxy group at position 8 of the quinolone ring. In the present study different analogues of gatifloxacin were prepared; the piperazinyl ring was chosen as the center of reaction for synthesizing this series of derivatives. The structures of these derivatives were established using spectroscopic techniques such as IR, H-1 NMR, and EIMS. In vitro antibacterial and antifungal activities were evaluated by disc diffusion method and these derivatives were compared with in-use fluoroquinolones like gatifloxacin, sparfloxacin, and gemifloxacin. Derivative A proved very potent against Gram-negative organisms, especially Pseudomonas aeruginosa, Shigella flexeneri, and Klebseilla pneumoniae, and derivatives A-C exhibited good antifungal activity compared to in-use quinolones. In addition, gatifloxacin and derivatives were investigated for immunomodulating activities. Derivative B has good anti-inflammatory activity, with IC50 < 12.5 mu g/ml.

  DOI：

  10.1007/s00044-009-9264-y

文献信息

• Synthesis, characterization, antibacterial, antifungal, and immunomodulating activities of gatifloxacin derivatives
  作者：Najma Sultana、Asia Naz、Bushra Khan、M. Saeed Arayne、M. Ahmed Mesaik

  DOI：10.1007/s00044-009-9264-y

  日期：2010.12

  Gatifloxacin is a synthetic broad-spectrum fluorquinolone antibacterial agent with a 3-methylpiperazinyl-side chain at position 7 and a methoxy group at position 8 of the quinolone ring. In the present study different analogues of gatifloxacin were prepared; the piperazinyl ring was chosen as the center of reaction for synthesizing this series of derivatives. The structures of these derivatives were established using spectroscopic techniques such as IR, H-1 NMR, and EIMS. In vitro antibacterial and antifungal activities were evaluated by disc diffusion method and these derivatives were compared with in-use fluoroquinolones like gatifloxacin, sparfloxacin, and gemifloxacin. Derivative A proved very potent against Gram-negative organisms, especially Pseudomonas aeruginosa, Shigella flexeneri, and Klebseilla pneumoniae, and derivatives A-C exhibited good antifungal activity compared to in-use quinolones. In addition, gatifloxacin and derivatives were investigated for immunomodulating activities. Derivative B has good anti-inflammatory activity, with IC50 < 12.5 mu g/ml.