(R)-(7-(methoxymethoxy)chroman-2-yl)methanol | 1526935-01-2

• 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)-(7-(methoxymethoxy)chroman-2-yl)methanol
• 英文别名: [(2R)-7-(methoxymethoxy)-3,4-dihydro-2H-chromen-2-yl]methanol
• CAS: 1526935-01-2
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: FETYQXIBLPNXES-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(7-(methoxymethoxy)chroman-2-yl)methanol 在 吡啶 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 (R)-1-(4-(2-fluoroethoxy)phenyl)-4-((7-(methoxymethoxy)chroman-2-yl)methyl)piperazine
  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 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到(R)-(7-(methoxymethoxy)chroman-2-yl)methanol
  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