4-isothiocyanato-7-(triflouromethyl)quinoline

• 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: 4-isothiocyanato-7-(triflouromethyl)quinoline
• 英文别名: 4-Isothiocyanato-7-(trifluoromethyl)quinoline；4-isothiocyanato-7-(trifluoromethyl)quinoline
• 化学式: C₁₁H₅F₃N₂S
• 分子量: 254.235
• InChiKey: MENNUHSUIZYJQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-isothiocyanato-7-(triflouromethyl)quinoline 、 磺胺异噁唑 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以82%的产率得到(E)-N-(4-(N-(3,4-dimethylisoxazol-5-yl)sulfamoyl)phenyl)-N'-(7-(trifluoromethyl)quinolin-4-yl)carbamimidothioic acid
  参考文献：
  名称：

  Synthesis and anticancer activity of some novel trifluoromethylquinolines carrying a biologically active benzenesulfonamide moiety

  摘要：

  Several trifluoromethylquinoline derivatives containing a biologically active benzenesulfonamide moiety 2-14, 16, urea derivatives 15, 17, 4-isothiocyanate 18 and the corresponding carbamimidothioic acid derivatives 19-30, were synthesized from the strategic starting material 4-chloro-7-trifluoromethylquinoline 1. The structures of the newly synthesized compounds were elucidated on the basis of elemental and spectral analyses. All the prepared compounds were evaluated for their in vitro anticancer activity against various cancer cell lines. Most of the synthesized compounds showed good activity, especially compound 15 which exhibited higher activity than the reference drug doxorubicin. In order to suggest the mechanism of action for their cytotoxic activity, molecular docking for all synthesized compounds was done on the active site of PI3K and good results were obtained. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.048
• 作为产物：
  描述：

  4-氯-7-三氟甲基喹啉 、 silver thiocyanate 以 甲苯 为溶剂， 反应 12.0h， 以100%的产率得到4-isothiocyanato-7-(triflouromethyl)quinoline
  参考文献：
  名称：

  合成4-喹啉基异硫氰酸酯的新途径

  摘要：

  由相应的4-氯喹啉和硫氰酸银在回流的甲苯中以区域特异性方式合成4-喹啉异硫氰酸酯。通过简单的过滤和浓缩，以定量收率和高纯度（> 95％）分离出产物。讨论了反应性和反应机理。该新方法将提供合成功能化的4-喹啉基异硫氰酸酯所缺乏的新方法。

  DOI：

  10.1016/j.tetlet.2006.01.119

文献信息

• Synthesis and anticancer activity of some novel trifluoromethylquinolines carrying a biologically active benzenesulfonamide moiety
  作者：Mohammed S. Al-Dosari、Mostafa M. Ghorab、Mansour S. AlSaid、Yassin M. Nissan、Abdulkareem B. Ahmed

  DOI：10.1016/j.ejmech.2013.08.048

  日期：2013.11

  Several trifluoromethylquinoline derivatives containing a biologically active benzenesulfonamide moiety 2-14, 16, urea derivatives 15, 17, 4-isothiocyanate 18 and the corresponding carbamimidothioic acid derivatives 19-30, were synthesized from the strategic starting material 4-chloro-7-trifluoromethylquinoline 1. The structures of the newly synthesized compounds were elucidated on the basis of elemental and spectral analyses. All the prepared compounds were evaluated for their in vitro anticancer activity against various cancer cell lines. Most of the synthesized compounds showed good activity, especially compound 15 which exhibited higher activity than the reference drug doxorubicin. In order to suggest the mechanism of action for their cytotoxic activity, molecular docking for all synthesized compounds was done on the active site of PI3K and good results were obtained. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Novel route to the synthesis of 4-quinolyl isothiocyanates
  作者：Boyu Zhong、Rima S. Al-Awar、Chuan Shih、John H. Grimes、Michal Vieth、Chafiq Hamdouchi

  DOI：10.1016/j.tetlet.2006.01.119

  日期：2006.3

  4-Quinolyl isothiocyanates were synthesized in a regiospecific fashion from the corresponding 4-chloroquinolines and silver thiocyanate in refluxing toluene. The products were isolated in quantitative yield and high purity (>95%) by simple filtration and concentration. Reactivity and mechanism of the reaction are discussed. The new approach would provide a new mean which had been lacking for the synthesis

  由相应的4-氯喹啉和硫氰酸银在回流的甲苯中以区域特异性方式合成4-喹啉异硫氰酸酯。通过简单的过滤和浓缩，以定量收率和高纯度（> 95％）分离出产物。讨论了反应性和反应机理。该新方法将提供合成功能化的4-喹啉基异硫氰酸酯所缺乏的新方法。