7,7'-(isophthaloylbis(piperazine-4,1-diyl))bis(1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid)

• 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: 7,7'-(isophthaloylbis(piperazine-4,1-diyl))bis(1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid)
• 英文别名: 7-[4-[3-[4-(3-Carboxy-1-cyclopropyl-6-fluoro-4-oxoquinolin-7-yl)piperazine-1-carbonyl]benzoyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid；7-[4-[3-[4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxoquinolin-7-yl)piperazine-1-carbonyl]benzoyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• 化学式: C₄₂H₃₈F₂N₆O₈
• 分子量: 792.796
• InChiKey: JMIUYBDJKVWMRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  58
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  环丙沙星 、 间苯二甲酰氯 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 以32%的产率得到7,7'-(isophthaloylbis(piperazine-4,1-diyl))bis(1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid)
  参考文献：
  名称：

  Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space

  摘要：

  We describe the synthesis and evaluation of a library of variably-linked ciprofloxacin dimers. These structures unify and expand on the use of fluoroquinolones as probes throughout the antibiotic literature. A dimeric analog (19) showed enhanced inhibition of its intracellular target (DNA gyrase), and translation to antibacterial activity in whole cells was demonstrated. Overall, cell permeation was governed by physicochemical properties and bacterial type. A principal component analysis demonstrated that the dimers occupy a unique and privileged region of chemical space most similar to the macrolide class of antibiotics. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.07.010

文献信息

• Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space
  作者：Audrey G. Ross、Bret M. Benton、Donovan Chin、Gianfranco De Pascale、John Fuller、Jennifer A. Leeds、Folkert Reck、Daryl L. Richie、Jason Vo、Matthew J. LaMarche

  DOI：10.1016/j.bmcl.2015.07.010

  日期：2015.9

  We describe the synthesis and evaluation of a library of variably-linked ciprofloxacin dimers. These structures unify and expand on the use of fluoroquinolones as probes throughout the antibiotic literature. A dimeric analog (19) showed enhanced inhibition of its intracellular target (DNA gyrase), and translation to antibacterial activity in whole cells was demonstrated. Overall, cell permeation was governed by physicochemical properties and bacterial type. A principal component analysis demonstrated that the dimers occupy a unique and privileged region of chemical space most similar to the macrolide class of antibiotics. (C) 2015 Elsevier Ltd. All rights reserved.