(S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide | 1187363-41-2

• 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-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide
• 英文别名: (2S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide
• CAS: 1187363-41-2
• 化学式: C₂₄H₄₀N₂O₂
• 分子量: 388.594
• InChiKey: APYXVASDIFELRE-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以57.5%的产率得到(S)-2-(benzylamino)-3-hydroxy-N-tetradecylpropanamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Family of Novel Ceramide Analogues in Chemoresistant Breast Cancer Cells

  摘要：

  Resistance to chemotherapy and endocrine therapy is a major cause of breast cancer treatment failure. We have synthesized six novel analogues using C8-ceramide as the lead analogue and studied their effect on hormone therapy resistant (MDA-MB-231) and chemoresistant (MCF-7TN-R) breast cancer cells. Pharmacologic intervention using these ceramide analogues inhibited clonogenic survival and induced apoptosis, with one analogue being more effective than C8-ceramide. Our results show ceramide-based therapy has therapeutic potential in treating drug resistant breast cancer.

  DOI：

  10.1021/jm9009668
• 作为产物：
  描述：

  苯甲醛 、 L-serine myristylamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以68.7%的产率得到(S)-2-(benzylideneamino)-3-hydroxy-N-tetradecylpropanamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Family of Novel Ceramide Analogues in Chemoresistant Breast Cancer Cells

  摘要：

  Resistance to chemotherapy and endocrine therapy is a major cause of breast cancer treatment failure. We have synthesized six novel analogues using C8-ceramide as the lead analogue and studied their effect on hormone therapy resistant (MDA-MB-231) and chemoresistant (MCF-7TN-R) breast cancer cells. Pharmacologic intervention using these ceramide analogues inhibited clonogenic survival and induced apoptosis, with one analogue being more effective than C8-ceramide. Our results show ceramide-based therapy has therapeutic potential in treating drug resistant breast cancer.

  DOI：

  10.1021/jm9009668

文献信息

• [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：WO2010093615A3

  公开（公告）日：2010-11-25
• Design, Synthesis, and Biological Activity of a Family of Novel Ceramide Analogues in Chemoresistant Breast Cancer Cells
  作者：James W. Antoon、Jiawang Liu、Matthew M. Gestaut、Matthew E. Burow、Barbara S. Beckman、Maryam Foroozesh

  DOI：10.1021/jm9009668

  日期：2009.9.24

  Resistance to chemotherapy and endocrine therapy is a major cause of breast cancer treatment failure. We have synthesized six novel analogues using C8-ceramide as the lead analogue and studied their effect on hormone therapy resistant (MDA-MB-231) and chemoresistant (MCF-7TN-R) breast cancer cells. Pharmacologic intervention using these ceramide analogues inhibited clonogenic survival and induced apoptosis, with one analogue being more effective than C8-ceramide. Our results show ceramide-based therapy has therapeutic potential in treating drug resistant breast cancer.