1-cyclopropyl-6-fluoro-7-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid | 1345888-27-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyclopropyl-6-fluoro-7-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-7-(4-naphthalen-1-ylsulfonylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 1345888-27-8
• 化学式: C₂₇H₂₄FN₃O₅S
• 分子量: 521.569
• InChiKey: SQGQWYBEUJTSBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  1-萘磺酰氯 、 环丙沙星 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.66h， 以87%的产率得到1-cyclopropyl-6-fluoro-7-(4-(naphthalen-1-ylsulfonyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design, synthesis and antibacterial activity of fluoroquinolones containing bulky arenesulfonyl fragment: 2D-QSAR and docking study

  摘要：

  Here in, we report the design, synthesis, and antibacterial activity of series of bulky arenesulfonamido derivatives using ciprofloxacin and norfloxacin as scaffolds. All the synthesized compounds were investigated in vitro for their antibacterial activities against two Gram-positive and two Gram-negative organisms using dilution broth method. Among the tested compounds examined, compounds 3-7 showed significance difference from the standard drug ciprofloxacin. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compound 3b into the active site of the topoisomerase II DNA-gyrase enzymes revealed a similar binding mode to ciprofloxacin with additional classical and nonclassical hydrogen bonds. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.09.011

文献信息

• Design, synthesis and antibacterial activity of fluoroquinolones containing bulky arenesulfonyl fragment: 2D-QSAR and docking study
  作者：Alaa A.-M. Abdel-Aziz、Yousif A. Asiri、Mohamed H.M. Al-Agamy

  DOI：10.1016/j.ejmech.2011.09.011

  日期：2011.11

  Here in, we report the design, synthesis, and antibacterial activity of series of bulky arenesulfonamido derivatives using ciprofloxacin and norfloxacin as scaffolds. All the synthesized compounds were investigated in vitro for their antibacterial activities against two Gram-positive and two Gram-negative organisms using dilution broth method. Among the tested compounds examined, compounds 3-7 showed significance difference from the standard drug ciprofloxacin. 2D-QSAR study provides details on the fine relationship linking structure and activity and offers clues for structural modifications that can improve the activity. Docking study of the compound 3b into the active site of the topoisomerase II DNA-gyrase enzymes revealed a similar binding mode to ciprofloxacin with additional classical and nonclassical hydrogen bonds. (C) 2011 Elsevier Masson SAS. All rights reserved.