7-(3,5-二甲基哌嗪-1-基)-6-氟-1-(2-氟苯基)-4-羰基-1,4-二氢喹啉-3-羧酸 | 164662-47-9

• 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: 7-(3,5-二甲基哌嗪-1-基)-6-氟-1-(2-氟苯基)-4-羰基-1,4-二氢喹啉-3-羧酸
• 英文名称: 7-(3,5-Dimethyl-piperazin-1-yl)-6-fluoro-1-(2-fluoro-phenyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 3-Quinolinecarboxylic acid, 7-(3,5-dimethyl-1-piperazinyl)-6-fluoro-1-(2-fluorophenyl)-1,4-dihydro-4-oxo-；7-(3,5-dimethylpiperazin-1-yl)-6-fluoro-1-(2-fluorophenyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 164662-47-9
• 化学式: C₂₂H₂₁F₂N₃O₃
• 分子量: 413.424
• InChiKey: BDFSBGNUJYQYMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.9
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,4,5-三氟苯甲酰乙酸乙酯 在 盐酸 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 生成 7-(3,5-二甲基哌嗪-1-基)-6-氟-1-(2-氟苯基)-4-羰基-1,4-二氢喹啉-3-羧酸
  参考文献：
  名称：

  Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria

  摘要：

  The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms. As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenylsubstituted derivatives to explore the effect of increasing lipophilicity on potency at this position. The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pK(a), and other attributes. The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M, tuberculosis activity. The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria. Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.

  DOI：

  10.1021/jm00015a021

文献信息

• Effect of Lipophilicity at N-1 on Activity of Fluoroquinolones against Mycobacteria
  作者：Thomas E. Renau、Joseph P. Sanchez、Martin A. Shapiro、Julie A. Dever、Stephen J. Gracheck、John M. Domagala

  DOI：10.1021/jm00015a021

  日期：1995.7

  The dramatic increase in drug resistant Mycobacterium tuberculosis has caused a resurgence in research targeted toward these organisms. As part of a systematic study to optimize the quinolone antibacterials against mycobacteria, we have prepared a series of N-1-phenylsubstituted derivatives to explore the effect of increasing lipophilicity on potency at this position. The compounds, synthesized by the modification of a literature procedure, were evaluated for activity against Gram-negative and Gram-positive bacteria, Mycobacterium fortuitum and Mycobacterium smegmatis, and the results correlated with log P, pK(a), and other attributes. The activity of the compounds against the rapidly growing, less hazardous organism M. fortuitum was used as a measure of M, tuberculosis activity. The results demonstrate that increasing lipophilic character by itself does not correlate with increased potency against mycobacteria. Rather, intrinsic activity against Gram-negative and/or Gram-positive bacteria is the governing factor for corresponding activity against mycobacteria.