6-氟-1-[甲基(氧代)-lambda5-氮烷基]-7-(4-甲基-1-哌嗪基)-4-氧代-1,4-二氢-3-喹啉羧酸 | 88569-53-3

• 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
• 中文名称: 6-氟-1-[甲基(氧代)-lambda5-氮烷基]-7-(4-甲基-1-哌嗪基)-4-氧代-1,4-二氢-3-喹啉羧酸
• 中文别名: 磷酸)二氢2-羟基丙烷-1,3-二基二(氧代乙烯)二(,钠盐
• 英文名称: 6-fluoro-1,4-dihydro-1-(methylamino)-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid 4'-oxide
• 英文别名: Amifloxacin N-oxide；6-fluoro-1-(methylamino)-7-(4-methyl-4-oxidopiperazin-4-ium-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 88569-53-3
• 化学式: C₁₆H₁₉FN₄O₄
• 分子量: 350.35
• InChiKey: KOHWXWKRVBJAQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  氨氟沙星 在 sodium hydroxide 、 palladium on activated charcoal 、 双氧水 作用下， 以82%的产率得到6-氟-1-[甲基(氧代)-lambda5-氮烷基]-7-(4-甲基-1-哌嗪基)-4-氧代-1,4-二氢-3-喹啉羧酸
  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

• 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).