(R)-N-[7-(methoxymethoxy)chroman-2-yl]methyl 4-iodobenzylamine | 1526935-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (R)-N-[7-(methoxymethoxy)chroman-2-yl]methyl 4-iodobenzylamine
• CAS: 1526935-26-1
• 化学式: C₁₉H₂₂INO₃
• 分子量: 439.293
• InChiKey: KHXINELXQKGVRQ-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.76
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  39.72
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-N-[7-(methoxymethoxy)chroman-2-yl]methyl 4-iodobenzylamine 在 盐酸 作用下， 以 1,4-二氧六环 、 异丙醇 为溶剂， 反应 3.0h， 以80%的产率得到(R)-2-[(4-iodobenzylamino)methyl]chroman-7-ol
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Series of Agonist Compounds as Potential Radiopharmaceuticals for Imaging Dopamine D_2/3 Receptors in Their High-Affinity State

  摘要：

  Imaging of dopamine D-2/3 receptors (D2/3R) can shed light on the nature of several neuropsychiatric disorders in which dysregulation of D2/3R signaling is involved. Agonist D-2/3 tracers for PET/SPECT imaging are considered to be superior to antagonists because they are more sensitive to dopamine concentrations and may selectively label the high-affinity receptor state. Carbon-11-labeled D2/3R agonists have been developed, but these short-lived tracers can be used only in centers with a cyclotron. Here, we report the development of a series of novel D2R agonist compounds based on the 2-aminomethylchromane (AMC) scaffold that provides ample opportunities for the introduction of longer-lived [F-18] or [I-123]. Binding experiments showed that several AMC compounds have a high affinity and selectivity for D2/3R and act as agonists. Two fluorine-containing compounds were [18(F)]-labeled, and both displayed specific binding to striatal D2/3R in rat brain slices in vitro. These findings encourage further in vivo evaluations.

  DOI：

  10.1021/jm401384w
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以766 mg的产率得到(R)-N-[7-(methoxymethoxy)chroman-2-yl]methyl 4-iodobenzylamine
  参考文献：
  名称：

  Synthesis and Characterization of a Novel Series of Agonist Compounds as Potential Radiopharmaceuticals for Imaging Dopamine D_2/3 Receptors in Their High-Affinity State

  摘要：

  Imaging of dopamine D-2/3 receptors (D2/3R) can shed light on the nature of several neuropsychiatric disorders in which dysregulation of D2/3R signaling is involved. Agonist D-2/3 tracers for PET/SPECT imaging are considered to be superior to antagonists because they are more sensitive to dopamine concentrations and may selectively label the high-affinity receptor state. Carbon-11-labeled D2/3R agonists have been developed, but these short-lived tracers can be used only in centers with a cyclotron. Here, we report the development of a series of novel D2R agonist compounds based on the 2-aminomethylchromane (AMC) scaffold that provides ample opportunities for the introduction of longer-lived [F-18] or [I-123]. Binding experiments showed that several AMC compounds have a high affinity and selectivity for D2/3R and act as agonists. Two fluorine-containing compounds were [18(F)]-labeled, and both displayed specific binding to striatal D2/3R in rat brain slices in vitro. These findings encourage further in vivo evaluations.

  DOI：

  10.1021/jm401384w