4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 6-chloro-5-nitro-4-oxidobenzofuroxan

• 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: 4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 6-chloro-5-nitro-4-oxidobenzofuroxan
• 英文别名: 6-Chloro-5-nitro-1-oxido-2,1,3-benzoxadiazol-1-ium-4-ol;1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid；6-chloro-5-nitro-1-oxido-2,1,3-benzoxadiazol-1-ium-4-ol;1-cyclopropyl-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid
• 化学式: C₆H₂ClN₃O₅*C₁₇H₁₈FN₃O₃
• 分子量: 562.899
• InChiKey: XFFUPMJGYPTFNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  39
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  190
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  4,6-dichloro-5-nitrobenzofuroxan 、 环丙沙星 在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以68%的产率得到4-(3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium 6-chloro-5-nitro-4-oxidobenzofuroxan
  参考文献：
  名称：

  Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones

  摘要：

  A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the compounds have been screened for antimicrobial and toxic activities. All resulting compounds retain high activity characteristic for fluoroquinolones. Many of the salts based on benzofuroxans and fluoroquinolones have higher activity than starting fluoroquinolones against Bacillus cereus 8035. Among the screened compounds, the compound 4d has shown the best antibacterial activity against B. cereus 8035, 8 times higher than the original Lomefloxacin (MBC value 1.5 mu g/mL). (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.03.086

文献信息

• Synthesis and biological evaluation of novel structural hybrids of benzofuroxan derivatives and fluoroquinolones
  作者：Elena Chugunova、Nurgali Akylbekov、Adelya Bulatova、Nikolai Gavrilov、Alexandra Voloshina、Natalia Kulik、Vladimir Zobov、Alexey Dobrynin、Victor Syakaev、Alexander Burilov

  DOI：10.1016/j.ejmech.2016.03.086

  日期：2016.6

  A series of novel hybrids based on benzofuroxan derivatives and fluoroquinolones (4a-d-6a-d) have been synthesized. Unexpectedly, the reactions have resulted in salt products formation during the hydrolysis of benzofuroxans by water molecules being present in the solvent instead of usual substitution products. All the compounds have been screened for antimicrobial and toxic activities. All resulting compounds retain high activity characteristic for fluoroquinolones. Many of the salts based on benzofuroxans and fluoroquinolones have higher activity than starting fluoroquinolones against Bacillus cereus 8035. Among the screened compounds, the compound 4d has shown the best antibacterial activity against B. cereus 8035, 8 times higher than the original Lomefloxacin (MBC value 1.5 mu g/mL). (C) 2016 Elsevier Masson SAS. All rights reserved.