N-Methoxy-N-methyl-arachidonamide | 229021-66-3

• 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: N-Methoxy-N-methyl-arachidonamide
• 英文别名: (5Z,8Z,11Z,14Z)-N-methoxy-N-methylicosa-5,8,11,14-tetraenamide
• CAS: 229021-66-3
• 化学式: C₂₂H₃₇NO₂
• 分子量: 347.541
• InChiKey: AGUQEYSQOOHOBF-GKFVBPDJSA-N

物化性质

• 沸点：
  436.0±55.0 °C(predicted)
• 密度：
  0.922±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Methoxy-N-methyl-arachidonamide 在 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.25h， 生成 (8Z,11Z,14Z,17Z)-1-Hydroxy-tricosa-8,11,14,17-tetraen-4-one
  参考文献：
  名称：

  Hemisynthesis and preliminary evaluation of novel endocannabinoid analogues

  摘要：

  Three new endocannabinoid analogues in which amide moiety was replaced either by oxomethylene group or ester moiety with simultaneous substitution of both alpha-hydrogens with methyl groups were synthesized and their abilities to interact with CB1-receptor and FAAH were investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00348-2
• 作为产物：
  描述：

  花生四烯酸 在 N-甲基吗啉 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 N-Methoxy-N-methyl-arachidonamide
  参考文献：
  名称：

  Hemisynthesis and preliminary evaluation of novel endocannabinoid analogues

  摘要：

  Three new endocannabinoid analogues in which amide moiety was replaced either by oxomethylene group or ester moiety with simultaneous substitution of both alpha-hydrogens with methyl groups were synthesized and their abilities to interact with CB1-receptor and FAAH were investigated. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00348-2

文献信息

• Inhibitors of fatty acid amide hydrolase
  申请人：The Scripps Research Institute

  公开号：US06462054B1

  公开（公告）日：2002-10-08

  Potent inhibitors of fatty acid amide hydrolase (FAAH) are constructed having Ki's below 200 pM and activities 102-103 times more potent than the corresponding trifluoromethyl ketones. The potent inhibitors combine several features, viz.: 1.) an &agr;-keto heterocylic head group; 2.) a hydrocarbon linkage unit employing an optimal C12-C8 chain length; and 3.) a phenyl or other &pgr;-unsaturation corresponding to the arachidonyl &Dgr;8.9/&Dgr;11.12 and/or oleyl &Dgr;9.10 positions. A preferred &agr;-keto heterocylic head group is &agr;-keto N4 oxazolopyridine, with incorporation of a second weakly basic nitrogen. Fatty acid amide hydrolase is an enzyme responsible for the degradation of oleamide (an endogenous sleep-inducing lipid) and anandamide (an endogenous ligand for cannabinoid receptors).

  具有Ki值低于200 pM且活性比相应的三氟甲基酮高102-103倍的脂肪酸酰胺水解酶（FAAH）的强效抑制剂已构建。这些强效抑制剂结合了几个特征，即：1.) 含有α-酮杂环头基团；2.) 使用最佳的C12-C8链长的烃链连接单元；以及3.) 含有苯环或其他与花生酸Δ8.9/Δ11.12和/或油酸Δ9.10位置相对应的π-不饱和度。首选的α-酮杂环头基团是α-酮N4噁唑吡啶，并且包含了第二个弱碱性氮原子。脂肪酸酰胺水解酶是一种负责降解油酰胺（一种内源性诱导睡眠的脂质）和阿南胺（一种内源性大麻素受体配体）的酶。
• INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Boger Dale L.

  公开号：US20090270421A1

  公开（公告）日：2009-10-29

  Potent inhibitors of fatty acid amide hydrolase (FAAH) are constructed having K i 's below 200 pM and activities 10 2 -10 3 times more potent than the corresponding trifluoromethyl ketones. The potent inhibitors combine several features, viz.: 1.) an α-keto heterocylic head group; 2.) a hydrocarbon linkage unit employing an optimal C12-C8 chain length; and 3.) a phenyl or other π-unsaturation corresponding to the arachidonyl Δ 8,9 /Δ 11,12 and/or oleyl Δ 9,10 positions. A preferred α-keto heterocylic head group is α-keto N4 oxazolopyridine, with incorporation of a second weakly basic nitrogen. Fatty acid amide hydrolase is an enzyme responsible for the degradation of oleamide (an endogenous sleep-inducing lipid) and anandamide (an endogenous ligand for cannabinoid receptors).

  具有Ki值低于200 pM的脂肪酸酰胺水解酶（FAAH）的强效抑制剂被构建出来，其活性比相应的三氟甲基酮高102-103倍。这些强效抑制剂结合了几个特征，即：1）α-酮杂环头基团；2）使用最佳C12-C8链长的烃链连接单元；和3）与花生四烯酸Δ8,9/Δ11,12和/或油酸Δ9,10位置相对应的苯基或其他π-不饱和度。首选的α-酮杂环头基团是α-酮N4噁唑吡啶，并结合第二个弱碱性氮。脂肪酸酰胺水解酶是一种酶，负责降解油酰胺（一种内源性诱导睡眠的脂质）和阿那达胺（一种内源性的大麻素受体配体）。
• Arachidonic acid amide inhibitors of gap junction cell-cell communication
  作者：Dale L. Boger、Haruhiko Sato、Aaron E. Lerner、Xiaojun Guan、Norton B. Gilula

  DOI：10.1016/s0960-894x(99)00148-1

  日期：1999.4

  A series of arachidonic acid amides including anandamide and arachidonamide that act as potent inhibitors of the rat glial cell gap junction is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
• US6462054B1
  申请人：——

  公开号：US6462054B1

  公开（公告）日：2002-10-08
• US6891043B2
  申请人：——

  公开号：US6891043B2

  公开（公告）日：2005-05-10