N-((5-(1H-benzo[d]imidazol-2-yl)-2-methylphenyl)carbamothioyl)-3,4-diethoxybenzamide

• 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: N-((5-(1H-benzo[d]imidazol-2-yl)-2-methylphenyl)carbamothioyl)-3,4-diethoxybenzamide
• 英文别名: N-[[5-(1H-benzimidazol-2-yl)-2-methylphenyl]carbamothioyl]-3,4-diethoxybenzamide
• 化学式: C₂₆H₂₆N₄O₃S
• 分子量: 474.583
• InChiKey: FRYUHZQZJUWGOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-二乙氧基苯甲酰氯 以 丙酮 为溶剂， 反应 2.0h， 生成 N-((5-(1H-benzo[d]imidazol-2-yl)-2-methylphenyl)carbamothioyl)-3,4-diethoxybenzamide
  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

文献信息

• Synthesis and structure–activity relationship of non-peptidic antagonists of neuropilin-1 receptor
  作者：Wang-Qing Liu、Valentino Megale、Lucia Borriello、Bertrand Leforban、Matthieu Montès、Elodie Goldwaser、Nohad Gresh、Jean-Philip Piquemal、Reda Hadj-Slimane、Olivier Hermine、Christiane Garbay、Françoise Raynaud、Yves Lepelletier、Luc Demange

  DOI：10.1016/j.bmcl.2014.07.028

  日期：2014.9

  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.