2-(2-fluoro-phenyl)-1H-imidazole-4,5-dicarbonitrile | 40953-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2-fluoro-phenyl)-1H-imidazole-4,5-dicarbonitrile
• 英文别名: 2-(2-fluorophenyl)-4,5-dicyanoimidazole；2-(2-Fluorophenyl)-1H-imidazole-4,5-dicarbonitrile
• CAS: 40953-38-6
• 化学式: C₁₁H₅FN₄
• 分子量: 212.186
• InChiKey: KAXOZCLWFSBEPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-fluoro-phenyl)-1H-imidazole-4,5-dicarbonitrile 在 二异丁基氢化铝 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 生成 2-(2-fluoro-phenyl)-5H-imidazo[4,5-d]pyridazine
  参考文献：
  名称：

  Imidazopyridazine Hepatitis C Virus Polymerase Inhibitors. Structure–Activity Relationship Studies and the Discovery of a Novel, Traceless Prodrug Mechanism

  摘要：

  By reducing the basicity of the core heterocycle in a series of HCV NS5B inhibitors, the hERG liability was reduced. The SAR was then systematically explored in order to increase solubility and enable dose escalation while retaining potency. During this exploration, a facile decarboxylation was noted and was exploited as a novel prodnig mechanism. The synthesis and characterization of these prodrugs and their utilization in chronic toxicity studies are presented.

  DOI：

  10.1021/jm401337x
• 作为产物：
  描述：

  2-氟苯甲醛 在 N-氯代丁二酰亚胺 、 硫酸 、 烟酰胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2-(2-fluoro-phenyl)-1H-imidazole-4,5-dicarbonitrile
  参考文献：
  名称：

  Imidazopyridazine Hepatitis C Virus Polymerase Inhibitors. Structure–Activity Relationship Studies and the Discovery of a Novel, Traceless Prodrug Mechanism

  摘要：

  By reducing the basicity of the core heterocycle in a series of HCV NS5B inhibitors, the hERG liability was reduced. The SAR was then systematically explored in order to increase solubility and enable dose escalation while retaining potency. During this exploration, a facile decarboxylation was noted and was exploited as a novel prodnig mechanism. The synthesis and characterization of these prodrugs and their utilization in chronic toxicity studies are presented.

  DOI：

  10.1021/jm401337x

文献信息

• Imidazoles and their compositions for plant growth regulation
  申请人：MAY & BAKER LIMITED

  公开号：EP0269238A1

  公开（公告）日：1988-06-01

  The invention provides a method of regulating the growth of a plant using a compound of the formula: wherein R¹ represents alkyl or phenyl optionally substituted by halogen, alkyl, alkoxy, alkylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, nitro, cyano, amino, carboxy, phenoxy, benzyloxy, alkoxycarbonyl, alkylamino, dialkylamino, alkanoylamino, R² represents nitro, cyano, carbamoyl or -CONR⁵R⁶ or -NR⁶COR⁵ (wherein R⁵ is as hereinbefore defined for R¹ and R⁶ represents hydrogen or alkyl), R³ represents halogen, nitro, cyano, amino, carbamoyl, -CONR⁷R⁸ (wherein R⁷ is as hereinbefore defined for R¹ and R⁸ represents hydrogen or alkyl), and R⁴ represents hydrogen or alkyl, or salts thereof with the exclusion of compounds in which R² and R³ simultaneously represent cyano groups; plant-growth regulating compositions, novel compounds and their preparation are described.

  该发明提供了一种利用以下化合物调节植物生长的方法：其中R¹代表烷基或苯基，可选择地取代为卤素、烷基氧基、烷基硫氧基、三氟甲基、三氟甲氧基、三氟甲基硫氧基、硝基、氰基、氨基、羧基、苯氧基、苄氧基、烷氧羰基、烷基氨基、二烷基氨基、烷酰氨基，R²代表硝基、氰基、氨基甲酰基或-CONR⁵R⁶或-NR⁶COR⁵（其中R⁵如前述定义的R¹，R⁶代表氢或烷基），R³代表卤素、硝基、氰基、氨基、氨基甲酰基、-CONR⁷R⁸（其中R⁷如前述定义的R¹，R⁸代表氢或烷基），R⁴代表氢或烷基，或其盐，排除R²和R³同时表示氰基团的化合物；描述了植物生长调节组合物、新化合物及其制备方法。
• Imidazopyridazine Hepatitis C Virus Polymerase Inhibitors. Structure–Activity Relationship Studies and the Discovery of a Novel, Traceless Prodrug Mechanism
  作者：Martin Leivers、John F. Miller、Stephanie A. Chan、Ryan Lauchli、Sebastian Liehr、Wenyan Mo、Tony Ton、Elizabeth M. Turner、Michael Youngman、J. Greg Falls、Susan Long、Amanda Mathis、Jill Walker

  DOI：10.1021/jm401337x

  日期：2014.3.13

  By reducing the basicity of the core heterocycle in a series of HCV NS5B inhibitors, the hERG liability was reduced. The SAR was then systematically explored in order to increase solubility and enable dose escalation while retaining potency. During this exploration, a facile decarboxylation was noted and was exploited as a novel prodnig mechanism. The synthesis and characterization of these prodrugs and their utilization in chronic toxicity studies are presented.