(Z)-1-(octadec-9-en-1-yl)-3-(3-methoxybenzyl)urea | 1450603-59-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-1-(octadec-9-en-1-yl)-3-(3-methoxybenzyl)urea
• 英文别名: 1-[(3-methoxyphenyl)methyl]-3-[(Z)-octadec-9-enyl]urea
• CAS: 1450603-59-4
• 化学式: C₂₇H₄₆N₂O₂
• 分子量: 430.674
• InChiKey: FWPHMCBZOHPJSY-KHPPLWFESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  31
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  50.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  油酸酰胺 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 生成 (Z)-1-(octadec-9-en-1-yl)-3-(3-methoxybenzyl)urea
  参考文献：
  名称：

  Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition

  摘要：

  Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 mu M). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 mu M). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.034

文献信息

• Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
  作者：Hui Wu、Charles J. Kelley、Alejandro Pino-Figueroa、Huyen D. Vu、Timothy J. Maher

  DOI：10.1016/j.bmc.2013.06.034

  日期：2013.9

  Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 mu M). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 mu M). (C) 2013 Elsevier Ltd. All rights reserved.