1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline
• 英文别名: 5-cyclopropyl-7-(4-ethylpiperazin-1-yl)-8-fluoro-2H-pyrazolo[4,3-c]quinolin-3-one
• 化学式: C₁₉H₂₂FN₅O
• 分子量: 355.415
• InChiKey: CVMXKORLAXAWPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  恩诺沙星 在 氯化亚砜 、 一水合肼 作用下， 反应 11.0h， 生成 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline
  参考文献：
  名称：

  Molecular structures of new ciprofloxacin derivatives

  摘要：

  Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate side chain and five-membered pyrazolo ring are almost coplanar with it. A piperazinyl ring exhibits a chair conformation. In the crystal packing of the carbamate analogue, two C-H...O interactions form a dimer. The pyrazolo derivative crystallises as solvate with 1.5 water molecules per quinoline molecule. In its crystal structure donor and acceptor functionalities form dimers, via hydrogen bonds, which are connected into an infinite pattern through hydrogen bonded water molecules. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-2860(02)00062-5

文献信息

• Molecular structures of new ciprofloxacin derivatives
  作者：Zrinka Banić Tomišić、Nedjeljko Kujundžić、Mirjana Bukvić Krajačić、Aleksandar Višnjevac、Biserka Kojić-Prodić

  DOI：10.1016/s0022-2860(02)00062-5

  日期：2002.6

  Two new derivatives from the ciprofloxacin fluoroquinoline family, 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-methylcarbamate and 1-cyclopropyl-7-(4-ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-(3-oxopyrazolo)[4,3-c]quinoline, were synthesised, tested for antibacterial activity and crystallised. Their molecular and crystal structures were determined. Tests in vitro reveal lower activities than for ciprofloxacin. Characteristic structural features of these compounds are comparable to data for other known fluoroquinolines. The bicyclic quinoline ring is planar in both compounds; the carbamate side chain and five-membered pyrazolo ring are almost coplanar with it. A piperazinyl ring exhibits a chair conformation. In the crystal packing of the carbamate analogue, two C-H...O interactions form a dimer. The pyrazolo derivative crystallises as solvate with 1.5 water molecules per quinoline molecule. In its crystal structure donor and acceptor functionalities form dimers, via hydrogen bonds, which are connected into an infinite pattern through hydrogen bonded water molecules. (C) 2002 Elsevier Science B.V. All rights reserved.