(5Z,8Z,11Z,14Z)-20-azidoeicosa-5,8,11,14-tetraenoic acid | 867281-04-7

• 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: (5Z,8Z,11Z,14Z)-20-azidoeicosa-5,8,11,14-tetraenoic acid
• 英文别名: (5Z,8Z,11Z,14Z)-20-azidoicosa-5,8,11,14-tetraenoic acid
• CAS: 867281-04-7
• 化学式: C₂₀H₃₁N₃O₂
• 分子量: 345.485
• InChiKey: MCQZYVOBBDAHTC-DTLRTWKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  51.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5Z,8Z,11Z,14Z)-20-azidoeicosa-5,8,11,14-tetraenoic acid 在 草酰氯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (5Z,8Z,11Z,14Z)-20-azidoeicosa-5,8,11,14-tetraenoic acid cyclopropylamide
  参考文献：
  名称：

  High Affinity Electrophilic and Photoactivatable Covalent Endocannabinoid Probes for the CB1 Receptor

  摘要：

  We have designed and synthesized the first two high affinity covalent anandamide probes for the CB1 receptor by introducing either an electrophilic isothiocyanato or a photoactivatable azido group at the terminal carbon of the arachidonic acid moiety. The headgroup of these anandamide analogues was optimized by using a cyclopropylamide substituent to impart optimal CB1 affinity. Both 20-isothiocyanato-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (1, AM3677) and 20-azido-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (2, AM3661) exhibited high selectivities for the CB 1 receptor with K-i values of 1.3 and 0.9 nM, respectively. Using suitable experimental conditions, both ligands were shown to covalently label the CB1 receptor with high efficiency. These two covalent probes for the endocannabinoid CB1 binding site open the door for exploring the ligand binding motifs involved in the activation of the CB1 receptor by its endogenous ligand, anandamide.

  DOI：

  10.1021/jm050272i
• 作为产物：
  描述：

  5-己炔酸甲酯 在 喹啉 、 lithium hydroxide 、 Lindlar's catalyst 、 copper(l) iodide 、 Zn(N3)2-2 pyr 、 四溴化碳 、 偶氮二甲酸二异丙酯 、 氢气 、 potassium carbonate 、 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 51.0h， 生成 (5Z,8Z,11Z,14Z)-20-azidoeicosa-5,8,11,14-tetraenoic acid
  参考文献：
  名称：

  High Affinity Electrophilic and Photoactivatable Covalent Endocannabinoid Probes for the CB1 Receptor

  摘要：

  We have designed and synthesized the first two high affinity covalent anandamide probes for the CB1 receptor by introducing either an electrophilic isothiocyanato or a photoactivatable azido group at the terminal carbon of the arachidonic acid moiety. The headgroup of these anandamide analogues was optimized by using a cyclopropylamide substituent to impart optimal CB1 affinity. Both 20-isothiocyanato-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (1, AM3677) and 20-azido-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (2, AM3661) exhibited high selectivities for the CB 1 receptor with K-i values of 1.3 and 0.9 nM, respectively. Using suitable experimental conditions, both ligands were shown to covalently label the CB1 receptor with high efficiency. These two covalent probes for the endocannabinoid CB1 binding site open the door for exploring the ligand binding motifs involved in the activation of the CB1 receptor by its endogenous ligand, anandamide.

  DOI：

  10.1021/jm050272i

文献信息

• High Affinity Electrophilic and Photoactivatable Covalent Endocannabinoid Probes for the CB1 Receptor
  作者：Chen Li、Wei Xu、Subramanian K. Vadivel、Pusheng Fan、Alexandros Makriyannis

  DOI：10.1021/jm050272i

  日期：2005.10.1

  We have designed and synthesized the first two high affinity covalent anandamide probes for the CB1 receptor by introducing either an electrophilic isothiocyanato or a photoactivatable azido group at the terminal carbon of the arachidonic acid moiety. The headgroup of these anandamide analogues was optimized by using a cyclopropylamide substituent to impart optimal CB1 affinity. Both 20-isothiocyanato-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (1, AM3677) and 20-azido-eicosa-5,8,11,14-tetraenoic acid cyclopropylamide (2, AM3661) exhibited high selectivities for the CB 1 receptor with K-i values of 1.3 and 0.9 nM, respectively. Using suitable experimental conditions, both ligands were shown to covalently label the CB1 receptor with high efficiency. These two covalent probes for the endocannabinoid CB1 binding site open the door for exploring the ligand binding motifs involved in the activation of the CB1 receptor by its endogenous ligand, anandamide.