(R)-1-(4-(2-(¹⁸F)fluoroethoxy)phenyl)-4-(4-(7-hydroxychroman-2-yl)-3-azabutyl)piperazine | 1526935-46-5

• 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-(¹⁸F)fluoroethoxy)phenyl)-4-(4-(7-hydroxychroman-2-yl)-3-azabutyl)piperazine
• 英文别名: (2R)-2-[[2-[4-[4-(2-(18F)fluoranylethoxy)phenyl]piperazin-1-yl]ethylamino]methyl]-3,4-dihydro-2H-chromen-7-ol
• CAS: 1526935-46-5
• 化学式: C₂₄H₃₂FN₃O₃
• 分子量: 428.536
• InChiKey: MSHUBKLFRWFTKI-XMIPQFJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-(4-苄氧基苯基)-哌嗪 在 盐酸 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 20.0~90.0 ℃ 、482.64 kPa 条件下， 反应 73.0h， 生成 (R)-1-(4-(2-(¹⁸F)fluoroethoxy)phenyl)-4-(4-(7-hydroxychroman-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