7-(4-Ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid | 88569-62-4

• 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-Ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid
• 英文别名: 7-(4-Ethylpiperazin-1-yl)-6-fluoro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid
• CAS: 88569-62-4
• 化学式: C₁₇H₂₁FN₄O₃
• 分子量: 348.377
• InChiKey: RCNVMGFKMNLTDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  76.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙基7-氯-6-氟-1-甲酰氨基-4-氧代-1,4-二氢-3-喹啉羧酸酯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 吡啶 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 7-(4-Ethyl-1-piperazinyl)-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid
  参考文献：
  名称：

  Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships

  摘要：

  A series of novel 3-quinolinecarboxylic acid derivatives have been prepared and their antibacterial activity evaluated. These derivatives are characterized by fluorine attached to the 6-position and substituted amino groups appended to the 1- and 7-positions. Structure-activity relationship studies indicate that antibacterial potency is greatest when the 1-substituent is methylamino and the 7-substituent is either 4-methyl-1-piperazinyl, 16, or 1-piperazinyl, 21. Derivatives 16 and 21, the 1-methylamino analogues of pefloxacin and norfloxacin, respectively, show comparable in vitro and in vivo antibacterial potency to these two known agents. The activity (vs. Escherichia coli Vogel) of 16 (amifloxacin) is the following: in vitro MIC (microgram/mL) = 0.25; in vivo (mice) PD50 (mg/kg) = 1.0 (po), 0.6 (sc).

  DOI：

  10.1021/jm00375a003

文献信息

• New quinolone compounds and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0090424B1

  公开（公告）日：1986-05-28
• US4499091A
  申请人：——

  公开号：US4499091A

  公开（公告）日：1985-02-12
• Novel amino-substituted 3-quinolinecarboxylic acid antibacterial agents: synthesis and structure-activity relationships
  作者：Mark P. Wentland、Denis M. Bailey、James B. Cornett、Richard A. Dobson、Ronald G. Powles、Roland B. Wagner

  DOI：10.1021/jm00375a003

  日期：1984.9

  A series of novel 3-quinolinecarboxylic acid derivatives have been prepared and their antibacterial activity evaluated. These derivatives are characterized by fluorine attached to the 6-position and substituted amino groups appended to the 1- and 7-positions. Structure-activity relationship studies indicate that antibacterial potency is greatest when the 1-substituent is methylamino and the 7-substituent is either 4-methyl-1-piperazinyl, 16, or 1-piperazinyl, 21. Derivatives 16 and 21, the 1-methylamino analogues of pefloxacin and norfloxacin, respectively, show comparable in vitro and in vivo antibacterial potency to these two known agents. The activity (vs. Escherichia coli Vogel) of 16 (amifloxacin) is the following: in vitro MIC (microgram/mL) = 0.25; in vivo (mice) PD50 (mg/kg) = 1.0 (po), 0.6 (sc).