3-amino-2-(4-fluorophenyl)quinolin-4-ol | 1219730-02-5

• 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: 3-amino-2-(4-fluorophenyl)quinolin-4-ol
• 英文别名: 3-Amino-2-(4-fluorophenyl)-1H-quinolin-4-one
• CAS: 1219730-02-5；876063-84-2
• 化学式: C₁₅H₁₁FN₂O
• 分子量: 254.264
• InChiKey: RMWXOAREIIVKPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-2-(4-fluorophenyl)quinolin-4-ol 、 间氯苯异氰酸酯 以 甲苯 为溶剂， 以94%的产率得到1-(3-chlorophenyl)-3-[2-(4-fluorophenyl)-4-hydroxyquinolin-3-yl]urea
  参考文献：
  名称：

  New 1,3-oxazolo[4,5-c]quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties

  摘要：

  A new class of fused oxazoloquinoline derivatives was synthesized starting from 2-bromo-1-phenylethanones 1a-b through multi-step reactions. The newly synthesized compounds were evaluated for their in vitro antibacterial against Escherichia coli (ATTC-25922), Staphylococcus aureus (ATTC-25923), Pseudomonas aeruginosa (ATCC-27853) and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Preliminary results indicated that most of the compounds demonstrated very good antibacterial and antituberculosis activities which are comparable with the first line drugs. Compounds 6a, 6c, 6g, 6j, 6k and 6n emerged as the lead antitubercular agents with MIC, 1 mu g/mL and 99% bacterial inhibition while eight compounds, viz.. 5a, 15k, 6a, 6c, 6g, 6j, 6k and 6n were found to be more potent than INN (MIC: 1.5 mu g/mL) with MIC 1 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.036
• 作为产物：
  描述：

  2-amino-N-(2-(4-fluorophenyl)-2-oxoethyl)benzamide 在 PPA 作用下， 反应 1.5h， 以99%的产率得到3-amino-2-(4-fluorophenyl)quinolin-4-ol
  参考文献：
  名称：

  由邻氨基苯甲酰胺制备3-氨基-2-苯基-4（1 H）-喹啉酮的一些新途径

  摘要：

  比较了制备3-氨基-2-苯基-4-1（H）-喹啉酮7a的几种新途径。最有效的方法是基于在（多）磷酸存在下苯甲酰邻氨基苯甲酰胺2a的环化作用。在孤立的杂环中间体的结构基础上讨论了所涉及的重排机理。验证了制备标题化合物7a的最佳方法，并制备了另外10种喹啉酮7。

  DOI：

  10.1021/jo051303k

文献信息

• Some New Routes for the Preparation of 3-Amino-2-phenyl-4(1<i>H</i>)-quinolinones from Anthranilamides
  作者：Pavel Hradil、Martin Grepl、Jan Hlaváč、Miroslav Soural、Michal Maloň、Valerio Bertolasi

  DOI：10.1021/jo051303k

  日期：2006.1.1

  Several new routes for the preparation of 3-amino-2-phenyl-4-1(H)-quinolinone 7a are compared. The most efficient is based on the cyclization of phenacyl anthranilamide 2a in the presence of (poly)phosphoric acid. The mechanisms of the rearrangements involved are discussed on the basis of the structures of isolated heterocyclic intermediates. The best methodology for the preparation of the title compound

  比较了制备3-氨基-2-苯基-4-1（H）-喹啉酮7a的几种新途径。最有效的方法是基于在（多）磷酸存在下苯甲酰邻氨基苯甲酰胺2a的环化作用。在孤立的杂环中间体的结构基础上讨论了所涉及的重排机理。验证了制备标题化合物7a的最佳方法，并制备了另外10种喹啉酮7。
• New 1,3-oxazolo[4,5-c]quinoline derivatives: Synthesis and evaluation of antibacterial and antituberculosis properties
  作者：Sumesh Eswaran、Airody Vasudeva Adhikari、R. Ajay Kumar

  DOI：10.1016/j.ejmech.2009.11.036

  日期：2010.3

  A new class of fused oxazoloquinoline derivatives was synthesized starting from 2-bromo-1-phenylethanones 1a-b through multi-step reactions. The newly synthesized compounds were evaluated for their in vitro antibacterial against Escherichia coli (ATTC-25922), Staphylococcus aureus (ATTC-25923), Pseudomonas aeruginosa (ATCC-27853) and Klebsiella pneumoniae (recultured) and antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC 27294). Preliminary results indicated that most of the compounds demonstrated very good antibacterial and antituberculosis activities which are comparable with the first line drugs. Compounds 6a, 6c, 6g, 6j, 6k and 6n emerged as the lead antitubercular agents with MIC, 1 mu g/mL and 99% bacterial inhibition while eight compounds, viz.. 5a, 15k, 6a, 6c, 6g, 6j, 6k and 6n were found to be more potent than INN (MIC: 1.5 mu g/mL) with MIC 1 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.