(S)-2-(2-methoxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide | 1239518-34-3

• 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: (S)-2-(2-methoxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide
• 英文别名: (2S)-3-hydroxy-2-[(2-methoxyphenyl)methylideneamino]-N-tetradecylpropanamide
• CAS: 1239518-34-3
• 化学式: C₂₅H₄₂N₂O₃
• 分子量: 418.62
• InChiKey: ZPHZQHRCPBYLBK-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  30
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-methoxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以78%的产率得到(S)-2-(2-methyoxybenzylamino)-3-hydroxy-N-tetradecylpropanamide
  参考文献：
  名称：

  Novel anti-viability ceramide analogs: Design, synthesis, and structure–activity relationship studies of substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides

  摘要：

  A group of novel L-serinamides, substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides (3a-o) and substituted (S)-2-(benzylamino)-3-hydroxy-N-tetradecyl propanamides (4c, 4i, 4l, and 4o), were synthesized as potential anti-tumor lead compounds. In vitro cell viability assay results indicate treatment with 3a-o compounds resulted in significant inhibition of cell viability in the chemo-resistant breast cancer cell line, MCF-7TN-R. Compounds 3i and 3l, both ortho-substituted analogs, show the greatest efficacy with IC50 values of 10.3 mu M and 12.5 mu M, respectively. The SAR analysis indicate that the imine functional group of 3a-o is critical for the cellular anti-viability effect, and the partial atomic charge (PAC) value of imine C atom is a valuable structural parameter for predicting the activity of these ceramide analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.044
• 作为产物：
  描述：

  邻甲氧基苯甲醛 、 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以72%的产率得到(S)-2-(2-methoxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide
  参考文献：
  名称：

  Novel anti-viability ceramide analogs: Design, synthesis, and structure–activity relationship studies of substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides

  摘要：

  A group of novel L-serinamides, substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides (3a-o) and substituted (S)-2-(benzylamino)-3-hydroxy-N-tetradecyl propanamides (4c, 4i, 4l, and 4o), were synthesized as potential anti-tumor lead compounds. In vitro cell viability assay results indicate treatment with 3a-o compounds resulted in significant inhibition of cell viability in the chemo-resistant breast cancer cell line, MCF-7TN-R. Compounds 3i and 3l, both ortho-substituted analogs, show the greatest efficacy with IC50 values of 10.3 mu M and 12.5 mu M, respectively. The SAR analysis indicate that the imine functional group of 3a-o is critical for the cellular anti-viability effect, and the partial atomic charge (PAC) value of imine C atom is a valuable structural parameter for predicting the activity of these ceramide analogs. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.044