ethyl 6,7-difluoro-1-hydroxymethyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate | 166381-41-5

• 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: ethyl 6,7-difluoro-1-hydroxymethyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
• 英文别名: ethyl 6,7-difluoro-1-(hydroxymethyl)-4-oxo-1H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
• CAS: 166381-41-5
• 化学式: C₁₄H₁₁F₂NO₄S
• 分子量: 327.308
• InChiKey: LIEDGWBWSJLZDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 6,7-difluoro-1-hydroxymethyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate 在 氢氧化钾 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 39.0h， 生成 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 71.0h， 生成 ethyl 6,7-difluoro-1-hydroxymethyl-4-oxo-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylate
  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

• QUINOLINECARBOXYLIC ACID DERIVATIVE AND PROCESS FOR PRODUCING THE SAME
  申请人：NIPPON SHINYAKU COMPANY, LIMITED

  公开号：EP0675127A1

  公开（公告）日：1995-10-04

  A quinolinecarboxylic acid derivative represented by general formula (I) and a pharmaceutically acceptable salt thereof, wherein z represents (un)substituted cyclic amino or phenyl; A represents > C=CH₂ or > CHR¹, R¹ representing flouroalkyl; R² represents hydrogen, alkyl, alkoxy, amino or halogen; and R³ represents hydrogen or alkyl. The invention compound is useful for treating various infectious diseases, in particular, those caused by Gram-positive bacteria including methicillin resistant Staphylococcus aureus and new quinolone and methicillin resistant resistant Staphylococcus aureus.

  通式(I)代表的喹啉羧酸衍生物及其药学上可接受的盐，其中z代表(未)取代的环氨基或苯基；A代表＞C＝CH₂或＞CHR¹，R¹代表氟代烷基；R²代表氢、烷基、烷氧基、氨基或卤素；R³代表氢或烷基。本发明化合物可用于治疗各种感染性疾病，特别是由革兰氏阳性细菌引起的疾病，包括耐甲氧西林金黄色葡萄球菌和新型喹诺酮类药物以及耐甲氧西林金黄色葡萄球菌。
• 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.