1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[[(3Z)-5-methyl-2-oxo-3-[4-(pyrimidin-2-ylsulfamoyl)phenyl]imino-indolin-1-yl]methyl]piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid | 895169-82-1

• 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: 1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[[(3Z)-5-methyl-2-oxo-3-[4-(pyrimidin-2-ylsulfamoyl)phenyl]imino-indolin-1-yl]methyl]piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[[5-methyl-2-oxo-3-[4-(pyrimidin-2-ylsulfamoyl)phenyl]iminoindol-1-yl]methyl]piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid
• CAS: 895169-82-1
• 化学式: C₃₉H₃₇FN₈O₇S
• 分子量: 780.837
• InChiKey: LHFNYUJGHADCSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  56
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  186
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 4-((5-methyl-2-oxoindolin-3-ylidene)amino)-N-(pyrimidin-2-yl)benzenesulfonamide 、 加替沙星 以 乙醇 为溶剂， 以71.8%的产率得到1-cyclopropyl-6-fluoro-8-methoxy-7-[3-methyl-4-[[(3Z)-5-methyl-2-oxo-3-[4-(pyrimidin-2-ylsulfamoyl)phenyl]imino-indolin-1-yl]methyl]piperazin-1-yl]-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Gatifloxacin derivatives: Synthesis, antimycobacterial activities, and inhibition of Mycobacterium tuberculosis DNA gyrase

  摘要：

  Sixteen 7-substituted gatifloxacin derivatives were synthesized and evaluated for antimycobacterial activity in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB) and multi-drug resistant M. tuberculosis (MDR-TB), and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. tuberculosis. Among the synthesized compounds, 1-cyclopropyl-6-fluoro-8-methoxy-7-[[[N-4-[I'-(5-isatinyl-beta-semicarbazo)]methyl]3-methyl]N-1-piperazinyl]-4-oxo-1,4-dihydro-3-quinoline carboxylic acid (3d) was found to be the most active compound in vitro with an MIC of 0.0125 mu g/mL against MTB and MTR-TB. In the in vivo animal model 3d decreased the bacterial load in lung and spleen tissues with 3.62- and 3.76-log 10 protections, respectively. Compound 3d was also found to be equally active as gatifloxacin in the inhibition of the supercoiling activity of wild-type M. tuberculosis DNA gyrase with an IC50 of 3.0 mu g/mL. The results demonstrate the potential and importance of developing new quinolone derivatives against mycobacterial infections. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.02.065