(4Z,7Z)-N-(3-hydroxypropyl)-9-(3-((2Z,5Z,8Z)-undeca-2,5,8-trien-1-yl)oxiran-2-yl)nona-4,7-dienamide

• 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: (4Z,7Z)-N-(3-hydroxypropyl)-9-(3-((2Z,5Z,8Z)-undeca-2,5,8-trien-1-yl)oxiran-2-yl)nona-4,7-dienamide
• 英文别名: (4Z,7Z)-N-(3-hydroxypropyI)-9-(3-((2Z,5Z,8Z)-undeca-2,5,8,trien-1-yI)oxiran-2yl)nona-4,7-dienamide；(4Z,7Z)-N-(3-hydroxypropyl)-9-[3-[(2Z,5Z,8Z)-undeca-2,5,8-trienyl]oxiran-2-yl]nona-4,7-dienamide
• 化学式: C₂₅H₃₉NO₃
• 分子量: 401.59
• InChiKey: BGSMYQXGSBZQKC-UQZHZJRSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  29
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二十二碳六烯酸 在 N-羟基丁二酰亚胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 1.33h， 生成 (4Z,7Z)-N-(3-hydroxypropyl)-9-(3-((2Z,5Z,8Z)-undeca-2,5,8-trien-1-yl)oxiran-2-yl)nona-4,7-dienamide
  参考文献：
  名称：

  Antitumorigenic Properties of Omega-3 Endocannabinoid Epoxides

  摘要：

  Accumulating studies have linked inflammation to tumor progression. Dietary omega-3 fatty acids, such as docosahexaenoic acid (DHA), have been shown to suppress tumor growth through their conversion to epoxide metabolites. Alternatively, DHA is converted enzymatically into docosahexaenoylethanolamide (DHEA), an endocannabinoid with antiproliferative activity. Recently, we reported a novel class of anti-inflammatory DHEA-epoxide derivative called epoxydocospentaenoic-ethanolamide (EDP-EA) that contain both ethanolamide and epoxide moieties. Herein, we study the antitumorigenic properties of EDP-EAs in an osteosarcoma (OS) model. First, we show similar to 80% increase in EDP-EAs in metastatic versus normal lungs of mice. We found significant differences in the apoptotic and antimigratory potencies of the different EDPEA regioisomers, which were partially mediated through cannabinoid receptor 1 (CB1). Next, we synthesized derivatives of the most pro-apoptotic regioisomer. These derivatives had reduced hydrolytic susceptibility to fatty acid amide hydrolase (FAAH) and increased CB1-selective binding. Collectively, we report a novel class of EDP-EAs that exhibit antiangiogenic, antitumorigenic, and antimigratory properties in OS.

  DOI：

  10.1021/acs.jmedchem.8b00243

文献信息

• [EN] DOCOSAHEXAENOIC ACID ENDOCANNABINOID EPOXIDE DERIVATIVE COMPOSITIONS<br/>[FR] COMPOSITIONS DÉRIVÉES D'ÉPOXYDE ENDOCANNABINOÏDE D'ACIDE DOCOSAHEXAÉNOÏQUE
  申请人：UNIV ILLINOIS

  公开号：WO2019060507A1

  公开（公告）日：2019-03-28

  The present disclosure provides novel compounds derived from docosahexaenoic acid endocannabinoid epoxides having anti-cancer, anti-inflammatory, anti-platelet aggregation and anti-angiogenic properties. Methods of synthesizing and using the compositions are also provided.

  本公开提供了从二十二碳六烯酸内源性大麻素环氧化物中衍生出的新化合物，具有抗癌、抗炎、抗血小板聚集和抗血管生成的特性。还提供了合成和使用这些组合物的方法。
• DOCOSAHEXAENOIC ACID ENDOCANNABINOID EPOXIDE DERIVATIVE COMPOSITIONS
  申请人：The Board of Trustees of the University of Illinois

  公开号：US20200247776A1

  公开（公告）日：2020-08-06

  The present disclosure provides novel compounds derived from docosahexaenoic acid endocamabinoid epoxides having anti-cancer, anti-inflammatory, anti-platelet aggregation and anti-angiogenic properties. Methods of synthesizing and using the compositions are also provided.