7-Chloro-1-(4-chloro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester | 98105-84-1

• 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: 7-Chloro-1-(4-chloro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 7-chloro-1-(4-chlorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylate
• CAS: 98105-84-1
• 化学式: C₁₈H₁₂Cl₂FNO₃
• 分子量: 380.203
• InChiKey: AIZWDJJRCYSIED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  7-Chloro-1-(4-chloro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 25.5h， 生成 1-(4-Chloro-phenyl)-6-fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003
• 作为产物：
  描述：

  (Z)-3-(4-Chloro-phenylamino)-2-(2,4-dichloro-5-fluoro-benzoyl)-acrylic acid ethyl ester 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 3.0h， 生成 7-Chloro-1-(4-chloro-phenyl)-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents

  摘要：

  A series of novel arylfluoroquinolones has been prepared. These derivatives are characterized by having a fluorine atom at the 6-position, substituted amino groups at the 7-position, and substituted phenyl groups at the 1-position. Structure-activity relationship (SAR) studies indicate that the in vitro antibacterial potency is greatest when the 1-substituent is either p-fluorophenyl or p-hydroxyphenyl and the 7-substituent is either 1-piperazinyl, 4-methyl-1-piperazinyl, or 3-amino-1-pyrrolidinyl. The electronic and spatial properties of the 1-substituent, as well as the steric bulk, play important roles in the antimicrobial potency in this class of antibacterials. As a result of this study, compounds 45 and 41 were found to possess excellent in vitro potency and in vivo efficacy.

  DOI：

  10.1021/jm00149a003