(5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 1-fluoromethyl-2-triisopropylsilanyloxy-ethyl ester | 886757-49-9

• 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: (5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 1-fluoromethyl-2-triisopropylsilanyloxy-ethyl ester
• CAS: 886757-49-9
• 化学式: C₃₃H₅₉FO₃Si
• 分子量: 550.914
• InChiKey: VYHFDUZPRDJZTK-YNJXCJHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.45
• 重原子数：
  38.0
• 可旋转键数：
  22.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 1-fluoromethyl-2-triisopropylsilanyloxy-ethyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 2-fluoro-1-hydroxymethyl-ethyl ester
  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
• 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 (5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 1-fluoromethyl-2-triisopropylsilanyloxy-ethyl ester
  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