7-chloro-1-phenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid | 98105-74-9

• 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-phenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid
• 英文别名: 7-chloro-6-fluoro-4-oxo-1-phenylquinoline-3-carboxylic acid
• CAS: 98105-74-9
• 化学式: C₁₆H₉ClFNO₃
• 分子量: 317.704
• InChiKey: ZPDINCURCCHBQE-UHFFFAOYSA-N

物化性质

• 熔点：
  271-273 °C
• 沸点：
  499.4±45.0 °C(Predicted)
• 密度：
  1.529±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-甲基哌嗪 、 7-chloro-1-phenyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid 以 various solvent(s) 为溶剂， 反应 24.0h， 生成 6-Fluoro-7-(4-methyl-piperazin-1-yl)-4-oxo-1-phenyl-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：

  2,4-二氯-5-氟-Β-氧代苯丙酸乙酯 在 sodium hydroxide 、 乙酸酐 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 7-chloro-1-phenyl-6-fluoro-1,4-dihydro-4-oxo-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

文献信息

• Intermediates for producing quinolone-3-carboxylic acids
  申请人：Abbott Laboratories

  公开号：US04994599A1

  公开（公告）日：1991-02-19

  A process for producing a 1,4-dihydro-4-oxo-quinoline-3-carboxylic acid by reacting an acctophenone with a dialkoxycarbonate to obtain the corresponding .beta.-ketoester, treating the .beta.-ketoester with a trialkylorthoformate in the presence of an acid anhydride followed by treatment with a substituted or unsubstituted amine to obtain the corresponding enaminoketoester, and then reacting the enaminoketoester with a strong base to obtain the corresponding quinoline-3-carboxylic acid ester. The acid ester may then be hydrolyzed, if desired, to obtain the quinoline-3-carboxylic acid. Also disclosed herein are compounds useful as intermediates useful in the production of quinoline-3-carboxylic acid.

  一种生产1,4-二氢-4-氧代喹啉-3-羧酸的方法，包括将乙酰苯与双烷氧基碳酸酯反应以获得相应的β-酮酸酯，将β-酮酸酯在酸酐存在下与三烷基正酸酐处理，然后使用取代或未取代的胺处理以获得相应的烯胺酮酸酯，最后使用强碱反应烯胺酮酸酯以获得相应的喹啉-3-羧酸酯。如果需要，酸酯可以水解以获得喹啉-3-羧酸。本文还公开了用于生产喹啉-3-羧酸的中间体化合物。
• US4730000
  申请人：——

  公开号：——

  公开（公告）日：——
• Quinoline antibacterial compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0131839B1

  公开（公告）日：1989-02-01
• CHU, DANIEL T.
  作者：CHU, DANIEL T.

  DOI：——

  日期：——
• CHU, D. T. W.;FERNANDES, P. B.;CLAIBORNE, A. K.;PIHULEAC, E.;NRDEEN, C. W+, J. MED. CHEM., 1985, 28, N 11, 1558-1564
  作者：CHU, D. T. W.、FERNANDES, P. B.、CLAIBORNE, A. K.、PIHULEAC, E.、NRDEEN, C. W+

  DOI：——

  日期：——