N-(cyanomethyl)-8-phenyloctanamide | 1010096-87-3

• 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: N-(cyanomethyl)-8-phenyloctanamide
• CAS: 1010096-87-3
• 化学式: C₁₆H₂₂N₂O
• 分子量: 258.363
• InChiKey: FGUJINPKSZFNMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(cyanomethyl)-8-phenyloctanamide 在 tri-n-butyltin azide 、 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.25h， 以79%的产率得到N-((1H-tetrazol-5-yl)methyl)-8-phenyloctanamide
  参考文献：
  名称：

  Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: A critical revisitation

  摘要：

  We have synthesized a series of 18 1,5- and 2,5-disubstituted carbamoyl tetrazoles, including LY2183240 (1) and LY2318912 (7), two compounds previously described as potent inhibitors of the cellular uptake of the endocannabinoid anandamide, and their regioisomers 2 and 8. We confirm that compound 1 is a potent inhibitor of both the cellular uptake and, like the other new compounds synthesized here, the enzymatic hydrolysis of anandamide. With the exception of 9, 12, 15, and the 2,5-regioisomer of LY2183240 2, the other compounds,were all found to be weakly active or inactive on anandamide uptake. Several compounds also inhibited the enzymatic hydrolysis of the other main endocannabinoid, 2-arachidonoylglycerol, as well as its enzymatic release from sn-1-oleoyl-2-arachidonoyl-glycerol, at submicromolar concentrations. Four of the novel compounds, i.e. 3, 4, 17, and 18, inhibited anandamide hydrolysis potently (IC(50) = 2.1-5.4 nM) and selectively over all the other targets tested (IC(50) >= 10 mu M), thus representing new potentially useful tools for the inhibition of fatty acid amide hydrolase. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.023
• 作为产物：
  描述：

  8-苯基辛酸 、 氨基乙腈硫酸氢盐 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.25h， 以47%的产率得到N-(cyanomethyl)-8-phenyloctanamide
  参考文献：
  名称：

  Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: A critical revisitation

  摘要：

  We have synthesized a series of 18 1,5- and 2,5-disubstituted carbamoyl tetrazoles, including LY2183240 (1) and LY2318912 (7), two compounds previously described as potent inhibitors of the cellular uptake of the endocannabinoid anandamide, and their regioisomers 2 and 8. We confirm that compound 1 is a potent inhibitor of both the cellular uptake and, like the other new compounds synthesized here, the enzymatic hydrolysis of anandamide. With the exception of 9, 12, 15, and the 2,5-regioisomer of LY2183240 2, the other compounds,were all found to be weakly active or inactive on anandamide uptake. Several compounds also inhibited the enzymatic hydrolysis of the other main endocannabinoid, 2-arachidonoylglycerol, as well as its enzymatic release from sn-1-oleoyl-2-arachidonoyl-glycerol, at submicromolar concentrations. Four of the novel compounds, i.e. 3, 4, 17, and 18, inhibited anandamide hydrolysis potently (IC(50) = 2.1-5.4 nM) and selectively over all the other targets tested (IC(50) >= 10 mu M), thus representing new potentially useful tools for the inhibition of fatty acid amide hydrolase. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.023

文献信息

• Carbamoyl tetrazoles as inhibitors of endocannabinoid inactivation: A critical revisitation
  作者：Giorgio Ortar、Maria Grazia Cascio、Aniello Schiano Moriello、Mercedes Camalli、Enrico Morera、Marianna Nalli、Vincenzo Di Marzo

  DOI：10.1016/j.ejmech.2007.02.023

  日期：2008.1

  We have synthesized a series of 18 1,5- and 2,5-disubstituted carbamoyl tetrazoles, including LY2183240 (1) and LY2318912 (7), two compounds previously described as potent inhibitors of the cellular uptake of the endocannabinoid anandamide, and their regioisomers 2 and 8. We confirm that compound 1 is a potent inhibitor of both the cellular uptake and, like the other new compounds synthesized here, the enzymatic hydrolysis of anandamide. With the exception of 9, 12, 15, and the 2,5-regioisomer of LY2183240 2, the other compounds,were all found to be weakly active or inactive on anandamide uptake. Several compounds also inhibited the enzymatic hydrolysis of the other main endocannabinoid, 2-arachidonoylglycerol, as well as its enzymatic release from sn-1-oleoyl-2-arachidonoyl-glycerol, at submicromolar concentrations. Four of the novel compounds, i.e. 3, 4, 17, and 18, inhibited anandamide hydrolysis potently (IC(50) = 2.1-5.4 nM) and selectively over all the other targets tested (IC(50) >= 10 mu M), thus representing new potentially useful tools for the inhibition of fatty acid amide hydrolase. (C) 2007 Elsevier Masson SAS. All rights reserved.