(R)-1-(4-(2-fluoroethoxy)phenyl)-4-(4-(7-(methoxymethoxy)chroman-2-yl)-3-azabutyl)piperazine | 1526935-32-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (R)-1-(4-(2-fluoroethoxy)phenyl)-4-(4-(7-(methoxymethoxy)chroman-2-yl)-3-azabutyl)piperazine
• CAS: 1526935-32-9
• 化学式: C₂₆H₃₆FN₃O₄
• 分子量: 473.588
• InChiKey: LYBZJTSQEZVNAC-RUZDIDTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  34.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  55.43
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-(2-fluoroethoxy)phenyl)-4-(4-(7-(methoxymethoxy)chroman-2-yl)-3-azabutyl)piperazine 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 异丙醇 为溶剂， 反应 3.0h， 生成 (R)-1-(4-(2-fluoroethoxy)phenyl)-4-(4-(7-hydroxychroman-2-yl)-3-azabutyl)piperazine oxalic acid
  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：

  3,4-二氢-7-羟基-2H-1-苯并吡喃-2-羧酸乙酯 在 吡啶 、 锂硼氢 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (R)-1-(4-(2-fluoroethoxy)phenyl)-4-(4-(7-(methoxymethoxy)chroman-2-yl)-3-azabutyl)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