N-butanoyl norarachidonyl amide

• 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: N-butanoyl norarachidonyl amide
• 英文别名: N-[(4Z,7Z,10Z,13Z)-nonadeca-4,7,10,13-tetraenyl]butanamide
• 化学式: C₂₃H₃₉NO
• 分子量: 345.569
• InChiKey: TVEVVHHVLQUIBI-GKFVBPDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 二苯基膦叠氮化物 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 甲醇 、 甲苯 、 乙腈 、 苯 为溶剂， 反应 123.0h， 生成 N-butanoyl norarachidonyl amide
  参考文献：
  名称：

  Synthesis, cannabinoid receptor activity, and enzymatic stability of reversed amide derivatives of arachidonoyl ethanolamide

  摘要：

  Retroanandamide (2f) and its 10 analogues (la-e, 2a-e) were synthesized and evaluated for the cannabinoid receptor activation by a [S-35]GTP gamma S binding assay using rat cerebellar membranes, and Chinese hamster ovary cell membranes expressing human CB2 receptors. The primary goal of the study was to develop cannabinoid receptor agonists having improved enzymatic stability compared to endogenous N-arachidonoyl ethanolamide (AEA). Furthermore, by reversing the amide bond of AEA, the formation of arachidonic acid would be prevented. Finally, an effect of the carbonyl carbon position on the cannabinoid receptor activity was explored by synthesizing retroanandamide analogues having different chain lengths (la-e, C-19; 2a-f, C-20). All the synthesized compounds, except 2c, behaved as partial agonists for the both cannabinoid receptors. In rat brain homogenate, the reversed amides possessed significantly higher stability against FAAH induced degradation than AEA. Therefore, the reversed amide analogues of AEA may serve as enzymatically stable structural basis for the drug design based on the endogenous cannabinoids. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.03.051

文献信息

• Synthesis, cannabinoid receptor activity, and enzymatic stability of reversed amide derivatives of arachidonoyl ethanolamide
  作者：Teija Parkkari、Juha R. Savinainen、Katri H. Raitio、Susanna M. Saario、Laura Matilainen、Tuomas Sirviö、Jarmo T. Laitinen、Tapio Nevalainen、Riku Niemi、Tomi Järvinen

  DOI：10.1016/j.bmc.2006.03.051

  日期：2006.8

  Retroanandamide (2f) and its 10 analogues (la-e, 2a-e) were synthesized and evaluated for the cannabinoid receptor activation by a [S-35]GTP gamma S binding assay using rat cerebellar membranes, and Chinese hamster ovary cell membranes expressing human CB2 receptors. The primary goal of the study was to develop cannabinoid receptor agonists having improved enzymatic stability compared to endogenous N-arachidonoyl ethanolamide (AEA). Furthermore, by reversing the amide bond of AEA, the formation of arachidonic acid would be prevented. Finally, an effect of the carbonyl carbon position on the cannabinoid receptor activity was explored by synthesizing retroanandamide analogues having different chain lengths (la-e, C-19; 2a-f, C-20). All the synthesized compounds, except 2c, behaved as partial agonists for the both cannabinoid receptors. In rat brain homogenate, the reversed amides possessed significantly higher stability against FAAH induced degradation than AEA. Therefore, the reversed amide analogues of AEA may serve as enzymatically stable structural basis for the drug design based on the endogenous cannabinoids. (c) 2006 Elsevier Ltd. All rights reserved.