N-[(2-chloropyridin-5-yl)methyl]oleamide | 1450603-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[(2-chloropyridin-5-yl)methyl]oleamide
• 英文别名: (Z)-N-[(6-chloropyridin-3-yl)methyl]octadec-9-enamide
• CAS: 1450603-52-7
• 化学式: C₂₄H₃₉ClN₂O
• 分子量: 407.039
• InChiKey: JIAIJNCBLCMFJI-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  28
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  油酸 、 5-氨基甲基-2-氯吡啶 在 N,N'-羰基二咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以36%的产率得到N-[(2-chloropyridin-5-yl)methyl]oleamide
  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.