1,3-difluoro-2-propyl (S)-2-methylarachidonate

• 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: 1,3-difluoro-2-propyl (S)-2-methylarachidonate
• 英文别名: 1,3-difluoropropan-2-yl (2S,5Z,8Z,11Z,14Z)-2-methylicosa-5,8,11,14-tetraenoate
• 化学式: C₂₄H₃₈F₂O₂
• 分子量: 396.561
• InChiKey: PETXVIUBNRQRDS-AQNSPSBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  花生四烯酸 在 4-二甲氨基吡啶 、 过氧化氢,锂盐(1:1) 、 sodium hexamethyldisilazane 、 三甲基乙酰氯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1,3-difluoro-2-propyl (S)-2-methylarachidonate
  参考文献：
  名称：

  α-Methylated derivatives of 2-arachidonoyl glycerol: Synthesis, CB1 receptor activity, and enzymatic stability

  摘要：

  alpha-Methylated analogues of the endogenous cannabinoid, 2-arachidonoyl glycerol (2-AG), were synthesized aiming to the improved enzymatic stability of 2-AG. In addition, the CB1 activity properties of fluoro derivatives of 2-AG were studied. The CB1 receptor activity was determined by the [S-35]GTP gamma S binding assay, and the enzymatic stability of alpha-methylated analogues was determined in rat cerebellar membranes. The results indicate that even if the alpha-methylated 2-AG derivatives are slightly weaker CB1 receptor agonists than 2-AG, they are clearly more stable than 2-AG. In addition, the results showed that the replacement of the hydroxyl group(s) of 2-AG by fluorine does not improve the CB1 activity of 2-AG. (C) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.01.101

文献信息

• α-Methylated derivatives of 2-arachidonoyl glycerol: Synthesis, CB1 receptor activity, and enzymatic stability
  作者：Teija Parkkari、Mikko Myllymäki、Juha R. Savinainen、Susanna M. Saario、Joel A. Castillo-Meléndez、Jarmo T. Laitinen、Tapio Nevalainen、Ari M.P. Koskinen、Tomi Järvinen

  DOI：10.1016/j.bmcl.2006.01.101

  日期：2006.5

  alpha-Methylated analogues of the endogenous cannabinoid, 2-arachidonoyl glycerol (2-AG), were synthesized aiming to the improved enzymatic stability of 2-AG. In addition, the CB1 activity properties of fluoro derivatives of 2-AG were studied. The CB1 receptor activity was determined by the [S-35]GTP gamma S binding assay, and the enzymatic stability of alpha-methylated analogues was determined in rat cerebellar membranes. The results indicate that even if the alpha-methylated 2-AG derivatives are slightly weaker CB1 receptor agonists than 2-AG, they are clearly more stable than 2-AG. In addition, the results showed that the replacement of the hydroxyl group(s) of 2-AG by fluorine does not improve the CB1 activity of 2-AG. (C) 2006 Elsevier Ltd. All rights reserved.