6-Fluoro-1-(4-fluoro-phenyl)-7-morpholin-4-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 98106-29-7

• 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-fluoro-phenyl)-7-morpholin-4-yl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 6-Fluoro-1-(4-fluorophenyl)-7-morpholin-4-yl-4-oxoquinoline-3-carboxylic acid
• CAS: 98106-29-7
• 化学式: C₂₀H₁₆F₂N₂O₄
• 分子量: 386.355
• InChiKey: VBYVJSSJBFHEEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 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-fluoro-phenyl)-7-morpholin-4-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

• Quinoline antibacterial compounds
  申请人：ABBOTT LABORATORIES

  公开号：EP0131839A1

  公开（公告）日：1985-01-23

  Quinoline compounds having the formula: wherein R is an phenyl group or an aromatic heterocyclic group, Z is an aliphatic heterocyclic group or an amine, and R1 is hydrogen or a carboxy-protecting group. The compounds here disclosed have antibacterial properties.

  具有以下式子的喹啉化合物 其中 R 是苯基或芳香杂环基团，Z 是脂肪杂环基团或胺，R1 是氢或羧基保护基团。此处公开的化合物具有抗菌特性。
• Synthesis of norfloxacin analogues catalyzed by Lewis and Brönsted acids: An alternative pathway
  作者：Socorro Leyva、Hiram Hernández

  DOI：10.1016/j.jfluchem.2010.07.002

  日期：2010.10

  An alternative synthetic pathway to prepare norfloxacin analogues is presented. Three Lewis acids (CeCl3 center dot 7H(2)O, AlCl3 center dot 6H(2)O, ZnCl2) and one Bronsted acid (TsOH) were tested as catalysts in the preparation of 3,4-difluoroacrylate. Cyclization of this acrylate at 55 degrees C was achieved with the use of Eaton's reagent (P2O5/MeSO3H) a known Bronsted acid. The fluoroquinolone-boron complex presented high yields on C-7 nucleophilic substitution of the fluorine atom by different heterocyclic amines with low, medium and strong nucleophilic character. (C) 2010 Elsevier B.V. All rights reserved.
• 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：——
• US4730000A
  申请人：——

  公开号：US4730000A

  公开（公告）日：1988-03-08
• Synthesis and structure-activity relationships of novel arylfluoroquinolone antibacterial agents
  作者：Daniel T. W. Chu、Prabhavathi B. Fernandes、Akiyo K. Claiborne、Eva Pihuleac、Carl W. Nordeen、Robert E. Maleczka、Andre G. Pernet

  DOI：10.1021/jm00149a003

  日期：1985.11

  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.