(S)-2-(2-hydroxybenzylamino)-3-hydroxy-N-tetradecylpropanamide | 1239518-41-2

• 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-hydroxybenzylamino)-3-hydroxy-N-tetradecylpropanamide
• 英文别名: (2S)-3-hydroxy-2-[(2-hydroxyphenyl)methylamino]-N-tetradecylpropanamide
• CAS: 1239518-41-2
• 化学式: C₂₄H₄₂N₂O₃
• 分子量: 406.609
• InChiKey: BCSHMOMANFRYTE-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  29
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  81.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-2-(2-hydroxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以75%的产率得到(S)-2-(2-hydroxybenzylamino)-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

文献信息

• COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER
  申请人：Beckman Barbara S.

  公开号：US20120027844A1

  公开（公告）日：2012-02-02

  Compounds and their syntheses are disclosed herein. Compositions and pharmaceutical compositions comprising a compound are also described, and include compositions also comprising liposomes. Methods for the treatment of cancer in animals comprising administering a compound or a composition comprising a compound are also described.

  本文披露了化合物及其合成方法。还描述了包含化合物的组合物和药物组合物，其中包括还包含脂质体的组合物。还描述了用于治疗动物癌症的方法，包括给动物施用化合物或包含化合物的组合物。
• US8853452B2
  申请人：——

  公开号：US8853452B2

  公开（公告）日：2014-10-07
• [EN] COMPOUNDS, THEIR SYNTHESES, COMPOSITIONS, AND METHODS TO TREAT CANCER<br/>[FR] COMPOSÉS, LEURS SYNTHÈSES, LEURS COMPOSITIONS ET MÉTHODES POUR TRAITER LE CANCER
  申请人：TULANE UNIVERSITY

  公开号：WO2010093615A2

  公开（公告）日：2010-08-19

  Compounds and their syntheses are disclosed herein. Compositions and pharmaceutical compositions comprising a compound are also described, and include compositions also comprising liposomes. Methods for the treatment of cancer in animals comprising administering a compound or a composition comprising a compound are also described.
• Novel anti-viability ceramide analogs: Design, synthesis, and structure–activity relationship studies of substituted (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamides
  作者：Jiawang Liu、James W. Antoon、Adharsh Ponnapakkam、Barbara S. Beckman、Maryam Foroozesh

  DOI：10.1016/j.bmc.2010.05.044

  日期：2010.7

  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.