toluene-4-sulfonic acid, (R)-(7-(methoxymethoxy)chroman-2-yl)methyl ester | 1526935-02-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: toluene-4-sulfonic acid, (R)-(7-(methoxymethoxy)chroman-2-yl)methyl ester
• 英文别名: [(2R)-7-(methoxymethoxy)-3,4-dihydro-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 1526935-02-3
• 化学式: C₁₉H₂₂O₆S
• 分子量: 378.446
• InChiKey: KTPFQWWMAZJEBJ-QGZVFWFLSA-N

物化性质

• 沸点：
  538.7±50.0 °C(predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  toluene-4-sulfonic acid, (R)-(7-(methoxymethoxy)chroman-2-yl)methyl ester 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二甲基亚砜 、 异丙醇 为溶剂， 反应 51.0h， 生成 (R)-2-[(4-(4-fluorobutoxy)benzylamino)methyl]chroman-7-ol 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：

  ethyl 7-hydroxychromane-2-carboxylate 在 吡啶 、 锂硼氢 、 amano lipase from Pseudomonasfluorescens 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 aq. phosphate buffer 、 二氯甲烷 、 水 为溶剂， 反应 2.0h， 生成 toluene-4-sulfonic acid, (R)-(7-(methoxymethoxy)chroman-2-yl)methyl ester
  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