(5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 2-(2,2,2-trifluoro-acetoxy)-1-(2,2,2-trifluoro-acetoxymethyl)-ethyl ester | 886757-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 2-(2,2,2-trifluoro-acetoxy)-1-(2,2,2-trifluoro-acetoxymethyl)-ethyl ester
• CAS: 886757-44-4
• 化学式: C₂₈H₃₈F₆O₆
• 分子量: 584.597
• InChiKey: ADNBQEJDAUJKDZ-AQNSPSBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40.0
• 可旋转键数：
  19.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

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 2-(2,2,2-trifluoro-acetoxy)-1-(2,2,2-trifluoro-acetoxymethyl)-ethyl ester 在 吡啶 、 甲醇 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 以100%的产率得到(5Z,8Z,11Z,14Z)-(S)-2-Methyl-icosa-5,8,11,14-tetraenoic acid 2-hydroxy-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 2-(2,2,2-trifluoro-acetoxy)-1-(2,2,2-trifluoro-acetoxymethyl)-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