4-methylpentanoic acid (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester | 1072902-70-5

• 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: 4-methylpentanoic acid (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester
• 英文别名: [(2S)-1-[(2S,3S)-3-hexyl-4-oxooxetan-2-yl]tridecan-2-yl] 4-methylpentanoate
• CAS: 1072902-70-5
• 化学式: C₂₈H₅₂O₄
• 分子量: 452.718
• InChiKey: CXHBRYSNTUYIQW-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.5
• 重原子数：
  32
• 可旋转键数：
  22
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲基戊酸 、 (3S,4S)-3-己基-4-[(S)-2-羟基十三烷基]-2-氧杂环丁酮 在 N,N'-二环己基碳二亚胺 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以68%的产率得到4-methylpentanoic acid (1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester
  参考文献：
  名称：

  Tetrahydrolipstatin Analogues as Modulators of Endocannabinoid 2-Arachidonoylglycerol Metabolism

  摘要：

  formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Three of the novel compounds, i.e., 11, 13, and 15, inhibited 2-AG formation via the diacylglycerol lipase a (DAGL alpha) with IC50 values lower than 50 nM (IC50 of THL = 1 mu M) and were between 23- and 375-fold selective vs 2-AG hydrolysis by rnonoacylglycerol lipase (MAGL) Lis well as vs cannabinoid CB1 and CB2 receptors and anandamide hydrolysis by fatty acid amide hydrolase (FAAH). Three other THL analogues, i.e., 14, 16, and 18, were slightly more potent than THL against DAGL alpha and appreciably selective vs MAGL, CB receptors, and FAAH (15-26-fold). One compound, i.e., 8, was a potent inhibitor of MAGL-like activity (IC50 = 0.41 mu M), and relatively (similar to 7-fold) selective vs the other targets tested.

  DOI：

  10.1021/jm800978m

文献信息

• Tetrahydrolipstatin Analogues as Modulators of Endocannabinoid 2-Arachidonoylglycerol Metabolism
  作者：Giorgio Ortar、Tiziana Bisogno、Alessia Ligresti、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1021/jm800978m

  日期：2008.11.13

  formation or hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-AG). Three of the novel compounds, i.e., 11, 13, and 15, inhibited 2-AG formation via the diacylglycerol lipase a (DAGL alpha) with IC50 values lower than 50 nM (IC50 of THL = 1 mu M) and were between 23- and 375-fold selective vs 2-AG hydrolysis by rnonoacylglycerol lipase (MAGL) Lis well as vs cannabinoid CB1 and CB2 receptors and anandamide hydrolysis by fatty acid amide hydrolase (FAAH). Three other THL analogues, i.e., 14, 16, and 18, were slightly more potent than THL against DAGL alpha and appreciably selective vs MAGL, CB receptors, and FAAH (15-26-fold). One compound, i.e., 8, was a potent inhibitor of MAGL-like activity (IC50 = 0.41 mu M), and relatively (similar to 7-fold) selective vs the other targets tested.