N-[2-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]-1-cyclopropyl-6-fluoro-7-[4-(4-methoxyphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxamide | 1187831-58-8

• 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: N-[2-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]-1-cyclopropyl-6-fluoro-7-[4-(4-methoxyphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxamide
• CAS: 1187831-58-8
• 化学式: C₃₃H₃₁ClFN₅O₄S
• 分子量: 648.158
• InChiKey: VOWAOOHGTDCKKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  45
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-氯-6-氟-1-环丙基-1,4-二氢-4-氧-3-喹啉羧酸 在 氯化亚砜 、 hydrazine hydrate 、 三乙胺 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 吡啶 、 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 2.0h， 生成 N-[2-(4-chlorophenyl)-4-oxo-1,3-thiazolidin-3-yl]-1-cyclopropyl-6-fluoro-7-[4-(4-methoxyphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxamide
  参考文献：
  名称：

  Synthesis and antimicrobial study of fluoroquinolone-based 4-thiazolidinones

  摘要：

  The title compounds 2-substituted phenyl-3-{1-cyclopropyl-6-fluoro-7-[4-(4-methoxyphenylpiperazin-1-yl]-4-oxo-1,4-dihydroquinoline} carboxamido-1,3-thiazolidin-4-ones 6a-j have been synthesized from lead molecule 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 1; this reacted with thionyl chloride to give acid chloride 2 and with hydrazine hydrate to afford hydrazide 3. The hydrazide 3 on condensation with substituted aromatic aldehydes a-j gave Schiff base; these on reaction with N-(4-methoxyphenyl) piperazine and thioglycolic acid furnished title compounds 6a-j. All of the synthesized compounds have been established by elemental analysis. IR and NMR spectral data and have been screened for antifungal and antibacterial activities.

  DOI：

  10.1007/s00044-009-9228-2

文献信息

• Synthesis and antimicrobial study of fluoroquinolone-based 4-thiazolidinones
  作者：Navin B. Patel、Sarvil D. Patel

  DOI：10.1007/s00044-009-9228-2

  日期：2010.11

  The title compounds 2-substituted phenyl-3-1-cyclopropyl-6-fluoro-7-[4-(4-methoxyphenylpiperazin-1-yl]-4-oxo-1,4-dihydroquinoline} carboxamido-1,3-thiazolidin-4-ones 6a-j have been synthesized from lead molecule 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 1; this reacted with thionyl chloride to give acid chloride 2 and with hydrazine hydrate to afford hydrazide 3. The hydrazide 3 on condensation with substituted aromatic aldehydes a-j gave Schiff base; these on reaction with N-(4-methoxyphenyl) piperazine and thioglycolic acid furnished title compounds 6a-j. All of the synthesized compounds have been established by elemental analysis. IR and NMR spectral data and have been screened for antifungal and antibacterial activities.