N-tetradecyl-2-cyanoacetamide | 1160837-94-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-tetradecyl-2-cyanoacetamide
• 英文别名: 2-cyano-N-tetradecylacetamide
• CAS: 1160837-94-4
• 化学式: C₁₇H₃₂N₂O
• 分子量: 280.454
• InChiKey: UBJCCVKSGVMGPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基吲哚-3-甲醛 、 N-tetradecyl-2-cyanoacetamide 在 哌啶 作用下， 以 乙醇 为溶剂， 以45%的产率得到2-cyano-N-tetradecyl-3-(2-methyl-1H-indol-3-yl)acrylamide
  参考文献：
  名称：

  Inhibition of Dynamin Mediated Endocytosis by the Dynoles—Synthesis and Functional Activity of a Family of Indoles

  摘要：

  Screening identified two bisindolylmaleimides as 100 mu M inhibitors of the GTPase activity of dynamin I. Focused library approaches allowed development of indole-based dynamin inhibitors called dynoles. 100-Fold in vitro enhancement of potency was noted with the best inhibitor, 2-cyano-3-(1-(2-(dimethylamino)ethyl)- 1H-indol-3-yl)-N-octylacrylamide (dynole 34-2), a 1.3 +/- 0.3 mu M dynamin I inhibitor. Dynole 34-2 potently inhibited receptor mediated endocytosis (RME) internalization of Texas red-transferrin. The rank order of potency for a variety of dynole analogues on RME in U2OS cells matched their rank order for dynamin inhibition, suggesting that the mechanism of inhibition is via dynamin. Dynoles are the most active dynamin I inhibitors reported for in vitro or RME evaluations. Dynole 34-2 is 15-fold more active than dynasore against dynamin I and 6-fold more active against dynamin mediated RME (IC50 similar to 15 mu M; RME IC50 similar to 80 mu M). The dynoles represent a new series of tools to better probe endocytosis and dynamin-mediated trafficking events in a variety of cells.

  DOI：

  10.1021/jm900036m