2-({2,6-dichloro-4-[3,3-(1,4-butanediyl)triazeno]phenyl}imino)imidazolidine | 108294-56-0

• 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: 2-({2,6-dichloro-4-[3,3-(1,4-butanediyl)triazeno]phenyl}imino)imidazolidine
• 英文别名: N-[2,6-dichloro-4-(pyrrolidin-1-yldiazenyl)phenyl]-4,5-dihydro-1H-imidazol-2-amine
• CAS: 108294-56-0
• 化学式: C₁₃H₁₆Cl₂N₆
• 分子量: 327.216
• InChiKey: WJMFHCMXFVRNLY-UHFFFAOYSA-N

物化性质

• 熔点：
  214-215.5 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  461.1±55.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-({2,6-dichloro-4-[3,3-(1,4-butanediyl)triazeno]phenyl}imino)imidazolidine 在 sodium hydroxide 、 sodium iodide 、 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 para-iodoclonidine
  参考文献：
  名称：

  Radioiodinated p-iodoclonidine. A high-affinity probe for the .alpha.2-adrenergic receptor

  摘要：

  The chemical synthesis of 2-[(2,6-dichloro-4-iodophenyl)imino]imidazolidine (PIC) and its radioiodinated analogue [125I]PIC is described. PIC was synthesized from 2,6-dichloroaniline in five synthetic steps. This agent displayed a high affinity for the alpha 2-adrenergic receptor (IC50 = 1.5 nM) in competitive binding assays conducted with purified human platelet plasma membrane fractions. For the synthesis of radioiodinated PIC the triazene intermediate 11 was synthesized from 2,6-dichloro-4-nitroaniline in five synthetic steps. Acid-catalyzed decomposition of 11 with no-carrier-added Na125I afforded high specific activity [125I]PIC. In view of its high affinity for the alpha 2-adrenergic receptor, [125I]PIC is a potentially useful probe for studies in adrenergic pharmacology.

  DOI：

  10.1021/jm00390a021
• 作为产物：
  描述：

  N-(2,6-二氯-4-硝基苯基)-4,5-二氢-1H-咪唑-2-胺 在 盐酸 、 氢氧化钾 、 硫酸 、 铁粉 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 3.5h， 生成 2-({2,6-dichloro-4-[3,3-(1,4-butanediyl)triazeno]phenyl}imino)imidazolidine
  参考文献：
  名称：

  Radioiodinated p-iodoclonidine. A high-affinity probe for the .alpha.2-adrenergic receptor

  摘要：

  The chemical synthesis of 2-[(2,6-dichloro-4-iodophenyl)imino]imidazolidine (PIC) and its radioiodinated analogue [125I]PIC is described. PIC was synthesized from 2,6-dichloroaniline in five synthetic steps. This agent displayed a high affinity for the alpha 2-adrenergic receptor (IC50 = 1.5 nM) in competitive binding assays conducted with purified human platelet plasma membrane fractions. For the synthesis of radioiodinated PIC the triazene intermediate 11 was synthesized from 2,6-dichloro-4-nitroaniline in five synthetic steps. Acid-catalyzed decomposition of 11 with no-carrier-added Na125I afforded high specific activity [125I]PIC. In view of its high affinity for the alpha 2-adrenergic receptor, [125I]PIC is a potentially useful probe for studies in adrenergic pharmacology.

  DOI：

  10.1021/jm00390a021

文献信息

• Radioiodinated p-iodoclonidine. A high-affinity probe for the .alpha.2-adrenergic receptor
  作者：M. Van Dort、R. Neubig、R. E. Counsell

  DOI：10.1021/jm00390a021

  日期：1987.7

  The chemical synthesis of 2-[(2,6-dichloro-4-iodophenyl)imino]imidazolidine (PIC) and its radioiodinated analogue [125I]PIC is described. PIC was synthesized from 2,6-dichloroaniline in five synthetic steps. This agent displayed a high affinity for the alpha 2-adrenergic receptor (IC50 = 1.5 nM) in competitive binding assays conducted with purified human platelet plasma membrane fractions. For the synthesis of radioiodinated PIC the triazene intermediate 11 was synthesized from 2,6-dichloro-4-nitroaniline in five synthetic steps. Acid-catalyzed decomposition of 11 with no-carrier-added Na125I afforded high specific activity [125I]PIC. In view of its high affinity for the alpha 2-adrenergic receptor, [125I]PIC is a potentially useful probe for studies in adrenergic pharmacology.