(R)-N-((7-(methoxymethoxy)chroman-2-yl)methyl)phthalimide | 1526935-03-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (R)-N-((7-(methoxymethoxy)chroman-2-yl)methyl)phthalimide
• CAS: 1526935-03-4
• 化学式: C₂₀H₁₉NO₅
• 分子量: 353.375
• InChiKey: FMQRZJRPUKMULH-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-N-((7-(methoxymethoxy)chroman-2-yl)methyl)phthalimide 在 三乙酰氧基硼氢化钠 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.5h， 生成 (R)-N-[7-(methoxymethoxy)chroman-2-yl]methyl 4-hydroxybenzyl amine
  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：

  (R)-7-(methoxymethoxy)chroman-2-carboxylic acid ethyl ester 在 吡啶 、 锂硼氢 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 (R)-N-((7-(methoxymethoxy)chroman-2-yl)methyl)phthalimide
  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