3-(5'-fluorobenzimidazol-20-yl)coumarin | 1328880-80-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(5'-fluorobenzimidazol-20-yl)coumarin
• 英文别名: 3-(5'-fluorobenzimidazol-2'-yl)coumarin；3-(5-fluoro-1H-benzimidazol-2-yl)chromen-2-one；3-(6-fluoro-1H-benzimidazol-2-yl)chromen-2-one
• CAS: 1328880-80-3
• 化学式: C₁₆H₉FN₂O₂
• 分子量: 280.258
• InChiKey: ZNSJKAYPODQMTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  香豆素-3-羧酸乙酯 、 4-氟-1,2-苯二胺 在 磷酸 作用下， 以 水 为溶剂， 反应 8.0h， 以65%的产率得到3-(5'-fluorobenzimidazol-20-yl)coumarin
  参考文献：
  名称：

  Development of New Sulfur-Containing Conjugated Compounds as Anti-HCV Agents

  摘要：

  Various conjugated compounds containing a coumarin moiety and a heterocyclic nucleus were synthesized. Their activity against hepatitis C virus was tested on subgenomic replicon replication in Huh 5-2 cells. Some heterobicycle-coumarin conjugates with the -S-CH2-linker were found to possess appealing antiviral activities. The sulfur atom in these conjugated compounds was found to be an essential element to their antiviral activity.

  DOI：

  10.1080/10426507.2010.520284

文献信息

• Development of New Sulfur-Containing Conjugated Compounds as Anti-HCV Agents
  作者：Jih Ru Hwu、Shu-Yu Lin、Shwu-Chen Tsay、Raghunath Singha、Benoy Kumar Pal、Pieter Leyssen、Johan Neyts

  DOI：10.1080/10426507.2010.520284

  日期：2011.5.1

  Various conjugated compounds containing a coumarin moiety and a heterocyclic nucleus were synthesized. Their activity against hepatitis C virus was tested on subgenomic replicon replication in Huh 5-2 cells. Some heterobicycle-coumarin conjugates with the -S-CH2-linker were found to possess appealing antiviral activities. The sulfur atom in these conjugated compounds was found to be an essential element to their antiviral activity.
• Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus
  作者：Shwu-Chen Tsay、Jih Ru Hwu、Raghunath Singha、Wen-Chieh Huang、Yung Hsiung Chang、Ming-Hua Hsu、Fa-kuen Shieh、Chun-Cheng Lin、Kuo Chu Hwang、Jia-Cherng Horng、Erik De Clercq、Inge Vliegen、Johan Neyts

  DOI：10.1016/j.ejmech.2013.02.008

  日期：2013.5

  A new compound library that contained 20 hinged benzimidazole coumarin hybrids and their beta-D-ribofuranosides was established. The anti-hepatitis C virus (HCV) activity of all novel coumarin derivatives, which were obtained by use of organic synthetic methods, was tested. Two of these hybrids exhibited appealing EC50 values of as low as 3.0 and 5.5 mu M. The best selectivity index was 14. The incorporation of a D-ribofuranose into the hinged hybrids provided the corresponding nucleosides with the beta configuration, one of which inhibited HCV replication with an EC50 value of 20 mu M. Additionally, the structure activity relationship is elucidated on the basis of the functional groups that were attached to the nuclei of benzimidazole, coumarin, and ribofuranose of the hybrids. (C) 2013 Elsevier Masson SAS. All rights reserved.