1-[2-(4-fluorophenyl)-4-hydroxyquinolin-3-yl]-3-pentylurea | 1219730-27-4

• 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: 1-[2-(4-fluorophenyl)-4-hydroxyquinolin-3-yl]-3-pentylurea
• 英文别名: 1-[2-(4-fluorophenyl)-4-oxo-1H-quinolin-3-yl]-3-pentylurea
• CAS: 1219730-27-4
• 化学式: C₂₁H₂₂FN₃O₂
• 分子量: 367.423
• InChiKey: RRIBWKOQEPBJCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[2-(4-fluorophenyl)-4-hydroxyquinolin-3-yl]-3-pentylurea 在 三氯氧磷 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 2.0h， 以81%的产率得到4-(4-fluorophenyl)-N-pentyl[1,3]oxazolo[4,5-c]quinolin-2-amine
  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：

  异氰酸戊酯 、 3-amino-2-(4-fluorophenyl)quinolin-4-ol 以 甲苯 为溶剂， 以80%的产率得到1-[2-(4-fluorophenyl)-4-hydroxyquinolin-3-yl]-3-pentylurea
  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

文献信息

• 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.