ethyl 16-[(ethylcarbamoyl)amino]hexadecanoate | 1611446-57-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 16-[(ethylcarbamoyl)amino]hexadecanoate
• 英文别名: Ethyl 16-(ethylcarbamoylamino)hexadecanoate；ethyl 16-(ethylcarbamoylamino)hexadecanoate
• CAS: 1611446-57-1
• 化学式: C₂₁H₄₂N₂O₃
• 分子量: 370.576
• InChiKey: MHAMMQUSUFPDMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 16-[(ethylcarbamoyl)amino]hexadecanoate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 16-[(ethylcarbamoyl)amino]hexadecanoic acid
  参考文献：
  名称：

  Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

  摘要：

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

  DOI：

  10.1021/jm501083y
• 作为产物：
  描述：

  16-羟基棕榈酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 35.0h， 生成 ethyl 16-[(ethylcarbamoyl)amino]hexadecanoate
  参考文献：
  名称：

  Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells

  摘要：

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.

  DOI：

  10.1021/jm501083y

文献信息

• [EN] OMEGA-3 ANALOGUES<br/>[FR] ANALOGUES D'OMÉGA-3
  申请人：UNIV SYDNEY

  公开号：WO2014078895A1

  公开（公告）日：2014-05-30

  The present invention relates to new fatty acid analogues and to their use in cancer therapy, including antimetastatic therapy.

  本发明涉及新的脂肪酸类似物及其在癌症治疗中的使用，包括抗转移治疗。
• OMEGA-3 ANALOGUES
  申请人：The University of Sydney

  公开号：US20150322001A1

  公开（公告）日：2015-11-12

  The present invention relates to new fatty acid analogues and to their use in cancer therapy, including antimetastatic therapy.

  本发明涉及新的脂肪酸类似物及其在癌症治疗中的应用，包括抗转移治疗。
• Synthetic ω-3 Epoxyfatty Acids As Antiproliferative and Pro-apoptotic Agents in Human Breast Cancer Cells
  作者：Herryawan Ryadi Eziwar Dyari、Tristan Rawling、Kirsi Bourget、Michael Murray

  DOI：10.1021/jm501083y

  日期：2014.9.11

  ω-3-17,18-Epoxyeicosapentaenoic acid decreases cell proliferation and activates apoptosis, whereas its regioisomers stimulate growth. We evaluated synthetic ω-3 epoxides of saturated fatty acids as antiproliferative and pro-apoptotic agents in MDA-MB-231 breast cancer cells. The epoxides, but not their urea, amide, or carbamate isosteres, impaired ATP production, enhanced caspase-3 activity, and activated c-jun-N-terminal-kinase signaling, leading to cyclin D1 down-regulation and cell cycle arrest in G1-phase. Fatty acid ω-3 monoepoxides may represent a novel class of antitumor agents.