5-(6-Fluoro-1H-benzimidazol-2-yl)-2-methylbenzenamine | 1183825-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 5-(6-Fluoro-1H-benzimidazol-2-yl)-2-methylbenzenamine
• 英文别名: 5-(6-fluoro-1H-benzimidazol-2-yl)-2-methylaniline
• CAS: 1183825-72-0
• 化学式: C₁₄H₁₂FN₃
• 分子量: 241.268
• InChiKey: GJOUJVSZWWKPLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(6-Fluoro-1H-benzimidazol-2-yl)-2-methylbenzenamine 、 benzo[1,3]dioxole-5-carbonyl isothiocyanate 以 丙酮 为溶剂， 反应 1.0h， 生成 N-((5-(5-fluoro-1H-benzo[d]imidazol-2-yl)-2-methylphenyl)carbamothioyl)benzo[d][1,3]dioxole-5-carboxamide
  参考文献：
  名称：

  Synthesis and structure–activity relationship of non-peptidic antagonists of neuropilin-1 receptor

  摘要：

  Neuropilins (NRPs) are VEGF-A165 co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A165/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A165/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization.

  DOI：

  10.1016/j.bmcl.2014.07.028
• 作为产物：
  描述：

  4-甲基-3-硝基苯甲醛 、 4-氟-1,2-苯二胺 在 sodium meta bi sulfate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-(6-Fluoro-1H-benzimidazol-2-yl)-2-methylbenzenamine
  参考文献：
  名称：

  Synthesis and structure–activity relationship of non-peptidic antagonists of neuropilin-1 receptor

  摘要：

  Neuropilins (NRPs) are VEGF-A165 co-receptors over-expressed in tumor cells, and considered as targets in angiogenic-related pathologies. We previously identified compound 1, the first non-peptidic antagonist of the VEGF-A165/NRP binding, which exhibits in vivo anti-angiogenic and anti-tumor activities. We report here the synthesis and biological evaluations of new antagonists structurally-related to compound 1. Among these molecules, 4a, 4c and 4d show cytotoxic effects on HUVEC and MDA-MB-31 cells, and antagonize VEGF-A165/NRP-1 binding. This study confirmed our key structure-activity relationships hypothesis and paved the way to compound 1 'hit to lead' optimization.

  DOI：

  10.1016/j.bmcl.2014.07.028