6,7-Difluoro-4-oxo-1-o-tolyl-1,4-dihydro-quinoline-3-carboxylic acid | 1026984-41-7

• 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: 6,7-Difluoro-4-oxo-1-o-tolyl-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6,7-Difluoro-1-(2-methylphenyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 1026984-41-7
• 化学式: C₁₇H₁₁F₂NO₃
• 分子量: 315.276
• InChiKey: BQMBGIIVNKZECT-UHFFFAOYSA-N

物化性质

• 沸点：
  475.5±45.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6,7-Difluoro-4-oxo-1-o-tolyl-1,4-dihydro-quinoline-3-carboxylic acid 、 2,6-二甲基哌嗪 以 乙腈 为溶剂， 以92%的产率得到7-(3,5-Dimethyl-piperazin-1-yl)-6-fluoro-4-oxo-1-o-tolyl-1,4-dihydro-quinoline-3-carboxylic acid
  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
• 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 为溶剂， 生成 6,7-Difluoro-4-oxo-1-o-tolyl-1,4-dihydro-quinoline-3-carboxylic acid
  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