7-chloro-6-fluoro-1,4-dihydro-1-(1-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid | 105614-66-2

• 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-chloro-6-fluoro-1,4-dihydro-1-(1-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-Chloro-6-fluoro-1-(1-methylcyclopropyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 105614-66-2
• 化学式: C₁₄H₁₁ClFNO₃
• 分子量: 295.698
• InChiKey: ZMSKTQFDBZQVAP-UHFFFAOYSA-N

物化性质

• 沸点：
  458.0±45.0 °C(Predicted)
• 密度：
  1.565±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  哌嗪 、 7-chloro-6-fluoro-1,4-dihydro-1-(1-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid 在 吡啶 作用下， 反应 18.0h， 以52%的产率得到6-氟-1,4-二氢-1-(1-甲基环丙基)-4-氧代-7-(1-哌嗪基)-3-喹啉羧酸
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005
• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 氢氧化钾 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 4.5h， 生成 7-chloro-6-fluoro-1,4-dihydro-1-(1-methylcyclopropyl)-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives

  摘要：

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.

  DOI：

  10.1021/jm00123a005

文献信息

• 7-Amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsäuren, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel
  申请人：BAYER AG

  公开号：EP0198192A1

  公开（公告）日：1986-10-22

  Die Erfindung betrifft neue 7-Amino-1-(subst.cyclopropyl)-1,4-dihydro-4-oxo-3-chinolincarbonsäuren der Formel (I) in welcher X1, X2, R1, R2, R3, R4, R5 die in der Beschreibung angegebene Bedeutung haben, Verfahren zu ihrer Herstellung sowie diese enthaltende antibakterielle Mittel.

  本发明涉及新的 7-氨基-1-(亚环丙基)-1,4-二氢-4-氧代-3-喹啉羧酸（式 (I)，其中 X1、X2、R1、R2、R3、R4、R5 具有描述中给出的含义），涉及其制备工艺和含有它们的抗菌剂。
• Cyclopropylamine
  申请人：BAYER AG

  公开号：EP0300155A2

  公开（公告）日：1989-01-25

  Die Erfindung betrifft Cyclopropylamine, Zwischenprodukte zu deren Herstellung, Verfahren zu deren Herstellung und deren Verwendung zur Herstellung von 1-Cyclopropyl-chino­loncarbonsäuren.

  本发明涉及环丙胺、制备环丙胺的中间体、制备环丙胺的工艺及其在制备 1-环丙基喹啉羧酸中的用途。
• ——
  作者：SCHRIEWER M.、 GROHE K.、 ZEILER H. -J.、 METZGER K. G.

  DOI：——

  日期：——
• US4705788A
  申请人：——

  公开号：US4705788A

  公开（公告）日：1987-11-10
• Fluoronaphthyridines and quinolones as antibacterial agents. 1. Synthesis and structure-activity relationship of new 1-substituted derivatives
  作者：D. Bouzard、P. Di Cesare、M. Essiz、J. P. Jacquet、P. Remuzon、A. Weber、T. Oki、M. Masuyoshi

  DOI：10.1021/jm00123a005

  日期：1989.3

  A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated. These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position. As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin or ciprofloxacin. Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.