(all-Z)-eicosa-5,8,11,14-tetraenesulfonyl chloride | 615250-01-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 磺酰卤
• 英文名称: (all-Z)-eicosa-5,8,11,14-tetraenesulfonyl chloride
• 英文别名: arachidonylsulfonyl chloride；Arachidonylsulfonyl chloride；(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraene-1-sulfonyl chloride
• CAS: 615250-01-6
• 化学式: C₂₀H₃₃ClO₂S
• 分子量: 373.0
• InChiKey: ZICMETCIDFJOIK-DOFZRALJSA-N

物化性质

• 沸点：
  468.6±34.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (all-Z)-eicosa-5,8,11,14-tetraenesulfonyl chloride 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以94%的产率得到arachidonylsulfonyl fluoride
  参考文献：
  名称：

  Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors

  摘要：

  Arachidonylsulfonyl fluoride (3), reported here for the first time, is similar in potency to its known methyl arachidonylfluorophosphonate (2) analogue as an inhibitor of mouse brain fatty acid amide hydrolase activity (IC50 0.1 nM) and cannabinoid CBI agonist [H-3]CP 55,940 binding (IC50 304-530 nM). Interestingly, 3 is much more selective than 2 as an inhibitor for fatty acid amide hydrolase relative to acetylcholinesterase, butyrylcholinesterase and neuropathy target esterase. N-(2-Hydroxyethyl)arachidonylsulfonamide (4) is at least 2500-fold less potent than N-(2-hydroxyethyl)arachidonamide (anandamide) (1) at the CB1 agonist site. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00721-2
• 作为产物：
  描述：

  花生四烯酸 在 lithium aluminium tetrahydride 、 1,1-二溴乙烷 、 四溴化碳 、 magnesium 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 (all-Z)-eicosa-5,8,11,14-tetraenesulfonyl chloride
  参考文献：
  名称：

  Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors

  摘要：

  Arachidonylsulfonyl fluoride (3), reported here for the first time, is similar in potency to its known methyl arachidonylfluorophosphonate (2) analogue as an inhibitor of mouse brain fatty acid amide hydrolase activity (IC50 0.1 nM) and cannabinoid CBI agonist [H-3]CP 55,940 binding (IC50 304-530 nM). Interestingly, 3 is much more selective than 2 as an inhibitor for fatty acid amide hydrolase relative to acetylcholinesterase, butyrylcholinesterase and neuropathy target esterase. N-(2-Hydroxyethyl)arachidonylsulfonamide (4) is at least 2500-fold less potent than N-(2-hydroxyethyl)arachidonamide (anandamide) (1) at the CB1 agonist site. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00721-2

文献信息

• Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors
  作者：Yoffi Segall、Gary B. Quistad、Daniel K. Nomura、John E. Casida

  DOI：10.1016/s0960-894x(03)00721-2

  日期：2003.10

  Arachidonylsulfonyl fluoride (3), reported here for the first time, is similar in potency to its known methyl arachidonylfluorophosphonate (2) analogue as an inhibitor of mouse brain fatty acid amide hydrolase activity (IC50 0.1 nM) and cannabinoid CBI agonist [H-3]CP 55,940 binding (IC50 304-530 nM). Interestingly, 3 is much more selective than 2 as an inhibitor for fatty acid amide hydrolase relative to acetylcholinesterase, butyrylcholinesterase and neuropathy target esterase. N-(2-Hydroxyethyl)arachidonylsulfonamide (4) is at least 2500-fold less potent than N-(2-hydroxyethyl)arachidonamide (anandamide) (1) at the CB1 agonist site. (C) 2003 Elsevier Ltd. All rights reserved.