6-Fluoro-1-(4-methoxy-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 98106-21-9

• 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: 6-Fluoro-1-(4-methoxy-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-Fluoro-1-(4-methoxyphenyl)-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid
• CAS: 98106-21-9
• 化学式: C₂₂H₂₂FN₃O₄
• 分子量: 411.433
• InChiKey: DYLWZBRISXVESV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-Fluoro-1-(4-methoxy-phenyl)-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid 生成 6-Fluoro-1-(4-hydroxyphenyl)-7-(4-methyl-1-piperazinyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  NORITA, XIROKADZU;ONISI, JOSINORI;NITTA, ATSUSI;NAGAKI, XIDEHESI;KITAYAMA+

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2,4-二氯-5-氟苯甲酰基)-3-乙氧基丙烯酸乙酯 在 sodium hydroxide 、 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 29.0h， 生成 6-Fluoro-1-(4-methoxy-phenyl)-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

文献信息

• Antimicrobial 1-substituted Phenyl-4-oxoquinoline-3-carboxylic acid compounds
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0181521A1

  公开（公告）日：1986-05-21

  Novel compounds of the formula: wherein R1 is a group of the formula: (where R3 is hydrogen atom or an alkyl having 1 to 2 carbon atoms), or a group for the formula: R2 is a group of the formula: R4 is hydroxy, fluorine atom or an alkanoyloxy having 1 to 6 carbon atoms, R5 is hydrogen or fluorine atom, and X is hydrogen or fluorine atom, provided that when R1 is and X is hydrogen atom, R2 is not a group of the formula and pharmaceutically acceptable salts thereof, said compounds having excellent antimicrobial activity and hence being useful as an antimicrobial agent, and a pharmaceutical composition comprising as an active ingredient said compounds or a salt thereof in admixture with a pharmaceutically acceptable diluent or carrier.

  式的新型化合物，其中 R1 是式的基团：（其中 R3 是氢原子或具有 1 至 2 个碳原子的烷基），或式的基团：R2 是式的基团：R4 是羟基、氟原子或具有 1 至 6 个碳原子的烷酰氧基，R5 是氢原子或氟原子，X 是氢原子或氟原子，条件是当 R1 是且 X 是氢原子时，R2 不是式的基团及其药学上可接受的盐，所述化合物具有优异的抗菌活性，因此可用作抗菌剂，以及一种药物组合物，其活性成分包括与药学上可接受的稀释剂或载体混合的所述化合物或其盐。