6-Fluoro-1-methanesulfonyloxymethyl-7-(4-methyl-piperazin-1-yl)-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid ethyl ester | 256954-15-1

• 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: 6-Fluoro-1-methanesulfonyloxymethyl-7-(4-methyl-piperazin-1-yl)-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid ethyl ester
• 英文别名: ethyl 6-fluoro-7-(4-methylpiperazin-1-yl)-1-(methylsulfonyloxymethyl)-4-oxo-1H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
• CAS: 256954-15-1
• 化学式: C₂₀H₂₄FN₃O₆S₂
• 分子量: 485.557
• InChiKey: KCXPWEGKGQAPKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  6-Fluoro-1-methanesulfonyloxymethyl-7-(4-methyl-piperazin-1-yl)-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid ethyl ester 在 氢氧化钾 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.0h， 以0.493 g的产率得到6-fluoro-1-methylene-7-(4-methyl-1-piperazinyl)-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel 7-Substituted 6-Fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic Acid Derivatives

  摘要：

  A series of 7-substituted 6-fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives (2) and (3) was prepared and evaluated for antibacterial activity. These compounds were obtained by the treatment of the 1-methanesulfonyloxymethyl or 1-fluoromethyl thiazetoquinolone-3-carboxylates (12, 14 and 20) with potassium hydroxide. Compounds (2) and (3) showed excellent in vitro antibacterial activity against both gram-negative and gram-positive bacteria including quinolone and Methicillin-resistant Staphylococcus aureus.

  DOI：

  10.3987/com-99-8712
• 作为产物：
  描述：

  ethyl 6,7-difluoro-4-hydroxy-2-(methoxymethyl)thioquinoline-3-carboxylate 在 吡啶 、 盐酸 、 磺酰氯 、 硫酸 、 水 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 86.0h， 生成 6-Fluoro-1-methanesulfonyloxymethyl-7-(4-methyl-piperazin-1-yl)-4-oxo-4H-2-thia-8b-aza-cyclobuta[a]naphthalene-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel 7-Substituted 6-Fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic Acid Derivatives

  摘要：

  A series of 7-substituted 6-fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives (2) and (3) was prepared and evaluated for antibacterial activity. These compounds were obtained by the treatment of the 1-methanesulfonyloxymethyl or 1-fluoromethyl thiazetoquinolone-3-carboxylates (12, 14 and 20) with potassium hydroxide. Compounds (2) and (3) showed excellent in vitro antibacterial activity against both gram-negative and gram-positive bacteria including quinolone and Methicillin-resistant Staphylococcus aureus.

  DOI：

  10.3987/com-99-8712

文献信息

• Synthesis and Antibacterial Activity of Novel 7-Substituted 6-Fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic Acid Derivatives
  作者：Masato Matsuoka、Jun Segawa、Isao Aminoto、Yasushi Masui、Yoshifumi Tomii、Masahiko Kitano、Masahiro Kise

  DOI：10.3987/com-99-8712

  日期：——

  A series of 7-substituted 6-fluoro-1-methylene-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives (2) and (3) was prepared and evaluated for antibacterial activity. These compounds were obtained by the treatment of the 1-methanesulfonyloxymethyl or 1-fluoromethyl thiazetoquinolone-3-carboxylates (12, 14 and 20) with potassium hydroxide. Compounds (2) and (3) showed excellent in vitro antibacterial activity against both gram-negative and gram-positive bacteria including quinolone and Methicillin-resistant Staphylococcus aureus.