N-(4-azido-2,6-diethyl<3,5-(3)H2>phenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine | 121158-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-azido-2,6-diethyl<3,5-(3)H2>phenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine
• 英文别名: N-(4-azido-2,6-diethyl-3,5-ditritiophenyl)imidazolidin-2-imine
• CAS: 121158-56-3
• 化学式: C₁₃H₁₈N₆
• 分子量: 262.31
• InChiKey: REKFDIPXCOVRPB-PTGCLLIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  50.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,6-二乙基苯胺 在 palladium on activated charcoal 盐酸 、 sodium azide 、 超重氢 、 水 、 溴 、 硝酸 、 铁粉 、 溶剂黄146 、 sodium nitrite 、 三氯氧磷 作用下， 以 乙醇 、 水 、 溶剂黄146 、 三氟乙酸 为溶剂， 反应 14.17h， 生成 N-(4-azido-2,6-diethyl<3,5-(3)H2>phenyl)-4,5-dihydro-1H-imidazol-2(3H)-imine
  参考文献：
  名称：

  A probe for octopamine receptors. Synthesis of 2-[(4-azido-2,6-diethylphenyl)imino]imidazolidine and its tritiated derivative, a potent reversible irreversible activator of octopamine-sensitive adenylate cyclase

  摘要：

  In order to develop an irreversible ligand for octopamine receptors, a highly potent azido-substituted 2-(phenyl-imino)imidazolidine (NC-5Z, 8) and its tritiated derivative (3H-NC-5Z, 11) have been designed and synthesized. Under reversible-binding conditions, NC-5Z is 50-100-fold more potent than octopamine in activating octopamine-sensitive adenylate cyclase in a variety of tissues. After photolysis, 3H-NC-5Z binds irreversibly to cell membranes, and this binding is reduced by preincubation with octopamine agonists and antagonists but not by norepinephrine, dopamine, serotonin, or histamine. NC-5Z should be useful both as a potent reversible octopamine agonist and as an affinity probe for characterizing and isolating octopamine-receptor proteins.

  DOI：

  10.1021/jm00128a022

文献信息

• A probe for octopamine receptors. Synthesis of 2-[(4-azido-2,6-diethylphenyl)imino]imidazolidine and its tritiated derivative, a potent reversible irreversible activator of octopamine-sensitive adenylate cyclase
  作者：James A. Nathanson、Girts Kaugars

  DOI：10.1021/jm00128a022

  日期：1989.8

  In order to develop an irreversible ligand for octopamine receptors, a highly potent azido-substituted 2-(phenyl-imino)imidazolidine (NC-5Z, 8) and its tritiated derivative (3H-NC-5Z, 11) have been designed and synthesized. Under reversible-binding conditions, NC-5Z is 50-100-fold more potent than octopamine in activating octopamine-sensitive adenylate cyclase in a variety of tissues. After photolysis, 3H-NC-5Z binds irreversibly to cell membranes, and this binding is reduced by preincubation with octopamine agonists and antagonists but not by norepinephrine, dopamine, serotonin, or histamine. NC-5Z should be useful both as a potent reversible octopamine agonist and as an affinity probe for characterizing and isolating octopamine-receptor proteins.