(S)-2-(2-hydroxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide | 1239518-37-6

• 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-hydroxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide
• 英文别名: ceramide analog 315；(2S)-3-hydroxy-2-[(2-hydroxyphenyl)methylideneamino]-N-tetradecylpropanamide
• CAS: 1239518-37-6
• 化学式: C₂₄H₄₀N₂O₃
• 分子量: 404.593
• InChiKey: BPMYZGVPTAKPRU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  29
• 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：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  水杨醛 、 N-Boc-L-serine tetradecyl amide 在 三氟乙酸 作用下， 生成 (S)-2-(2-hydroxybenzylideneamino)-3-hydroxy-N-tetradecylpropanamide
  参考文献：
  名称：

  Inhibition of breast tumor growth in mice after treatment with ceramide analog 315

  摘要：

  The aim of this study was to evaluate the anticancer and antitumor activities of ceramide analog 315 in nude mice. Nude mice (n = 10) were injected bilaterally with 5 x 10(6) MDA-MB-231 cells on each side. Tumors were allowed to form for 2 weeks. The mice were then divided into two groups (n = 5 in each group). The control group mice were injected with 25 mu l of dimethyl sulfoxide and the treatment group mice were injected with 10 mg/kg of analog 315 (in dimethyl sulfoxide, 25 mu l volume) every day for a period of 3 weeks. Animal weights and tumors were measured every week for 3 weeks. At the end of the experimental period, control animals had retained excess fluid, and showed larger tumor sizes compared with the treated group (2.95 vs. 1.67g). A 45% reduction in tumor size and 80% decrease in tumor volume were observed in the treatment group. There was a significant increase in the weights of liver (10%) and spleen (19%) between the control and treated animals. Hematoxylin and Eosin staining of MDA-MB-231 tumor sections revealed more acellular necrotic regions in tumors from the treatment groups compared with the ones from the control group. Ki67, a proliferation marker was higher in number in control tumor section (71.8 +/- 12.8) compared to the treatment tumor section (37.4 +/- 10.4) (P < 0.001). Photomicrographs showed metastatic tumor burden in kidney, lungs, and spleen collected from the control group mice bearing MDA-MB-231 tumors. Treatment group mice showed normal microscopic tissue architecture. Overall, our study showed tumor growth inhibition and antimetastatic effects for the novel ceramide analog 315. Copyright (C) 2018 Wolters Kluwer Health, Inc. All rights reserved.

  DOI：

  10.1097/cad.0000000000000675