1-Cyclopropyl-2-ethylsulfanyl-6-fluoro-8-methoxy-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid | 1322062-50-9

• 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
• 英文名称: 1-Cyclopropyl-2-ethylsulfanyl-6-fluoro-8-methoxy-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• CAS: 1322062-50-9
• 化学式: C₂₀H₂₄FN₃O₄S
• 分子量: 421.493
• InChiKey: MDWGLOSEAYWKGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  在 硫酸 作用下， 反应 2.0h， 以5%的产率得到1-Cyclopropyl-2-ethylsulfanyl-6-fluoro-8-methoxy-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones

  摘要：

  Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.112

文献信息

• Synthesis and evaluation of 1-cyclopropyl-2-thioalkyl-8-methoxy fluoroquinolones
  作者：Kevin R. Marks、Muhammad Malik、Arkady Mustaev、Hiroshi Hiasa、Karl Drlica、Robert J. Kerns

  DOI：10.1016/j.bmcl.2011.05.112

  日期：2011.8

  Novel fluoroquinolone derivatives substituted with a 2-thioalkyl moiety, with and without a concomitant 3-carboxylate group, were synthesized to evaluate the effect of C-2 thioalkyl substituents on gyrase binding and inhibition. The presence of a 2-thioalkyl group universally decreased activity as compared to parent fluoroquinolones. However, with derivatives of moxifloxacin the presence of either a 2-thioalkyl group or a 3-carboxylate moiety increased activity over the 2,3-unsubstituted derivative. Energy minimization of structures provides an explanation for relative activities of fluoroquinolones having a C-2 thio moiety. (C) 2011 Elsevier Ltd. All rights reserved.