3-(5'-carboxybenzimidazol-20-yl)-6-nitrocoumarin | 1443122-75-5

• 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'-carboxybenzimidazol-20-yl)-6-nitrocoumarin
• 英文别名: 2-(6-nitro-2-oxo-chromen-3-yl)-1H-benzimidazole-5-carboxylic acid；2-(6-nitro-2-oxochromen-3-yl)-3H-benzimidazole-5-carboxylic acid
• CAS: 1443122-75-5
• 化学式: C₁₇H₉N₃O₆
• 分子量: 351.275
• InChiKey: GXJJJNLFQCVSSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  138
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  6-(羟基(氧代)氨基)-2-氧代-2H-苯并吡喃-3-羧酸乙酯 、 3,4-二氨基苯甲酸 在 磷酸 作用下， 以 水 为溶剂， 反应 8.0h， 以73%的产率得到3-(5'-carboxybenzimidazol-20-yl)-6-nitrocoumarin
  参考文献：
  名称：

  Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2013.02.008

文献信息

• 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.