(4-{2-[4-(2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-ylmethoxy)phenyl]vinyl}phenyl)methylcarbamic acid tert-butyl ester | 902143-15-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (4-{2-[4-(2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-ylmethoxy)phenyl]vinyl}phenyl)methylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[4-[(E)-2-[4-[(2,2-ditert-butyl-1,3,2-dioxasilinan-5-yl)methoxy]phenyl]ethenyl]phenyl]-N-methylcarbamate
• CAS: 902143-15-1
• 化学式: C₃₂H₄₇NO₅Si
• 分子量: 553.814
• InChiKey: KPDWTCVTGWDLNI-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.31
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-{2-[4-(2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-ylmethoxy)phenyl]vinyl}phenyl)methylcarbamic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以99%的产率得到(4-{2-[4-(3-hydroxy-2-hydroxymethylpropoxy)phenyl]vinyl}phenyl)methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  F-18 Stilbenes as PET Imaging Agents for Detecting β-Amyloid Plaques in the Brain

  摘要：

  Imaging agents targeting beta-amyloid (A beta) may be useful for diagnosis and treatment of patients with Alzheimer's disease (AD). Compounds 3e and 4e are fluorinated stilbene derivatives displaying high binding affinities for A beta plaques in AD brain homogenates (K-i = 15 +/- 6 and 5.0 +/- 1.2 nM, respectively). In vivo biodistributions of [F-18]3e and [F-18]4e in normal mice exhibited excellent brain penetrations (5.55 and 9.75% dose/g at 2 min), and rapid brain washouts were observed, especially for [F-18]4e (0.72% dose/g at 60 min). They also showed in vivo plaque labeling in APP/PS1 or Tg2576 transgenic mice, animal models for AD. Autoradiography of postmortem AD brain sections and AD homogenate binding studies confirmed the selective and specific binding properties to A beta plaques. In conclusion, the preliminary results strongly suggest that these fluorinated stilbene derivatives, [F-18]3e and [(18F)]4e, are suitable candidates as A beta plaque imaging agents for studying patients with AD.

  DOI：

  10.1021/jm050166g
• 作为产物：
  描述：

  (E)-4-methylamino-4'-hydroxystilbene 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 (4-{2-[4-(2,2-di-tert-butyl-[1,3,2]dioxasilinan-5-ylmethoxy)phenyl]vinyl}phenyl)methylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  F-18 Stilbenes as PET Imaging Agents for Detecting β-Amyloid Plaques in the Brain

  摘要：

  Imaging agents targeting beta-amyloid (A beta) may be useful for diagnosis and treatment of patients with Alzheimer's disease (AD). Compounds 3e and 4e are fluorinated stilbene derivatives displaying high binding affinities for A beta plaques in AD brain homogenates (K-i = 15 +/- 6 and 5.0 +/- 1.2 nM, respectively). In vivo biodistributions of [F-18]3e and [F-18]4e in normal mice exhibited excellent brain penetrations (5.55 and 9.75% dose/g at 2 min), and rapid brain washouts were observed, especially for [F-18]4e (0.72% dose/g at 60 min). They also showed in vivo plaque labeling in APP/PS1 or Tg2576 transgenic mice, animal models for AD. Autoradiography of postmortem AD brain sections and AD homogenate binding studies confirmed the selective and specific binding properties to A beta plaques. In conclusion, the preliminary results strongly suggest that these fluorinated stilbene derivatives, [F-18]3e and [(18F)]4e, are suitable candidates as A beta plaque imaging agents for studying patients with AD.

  DOI：

  10.1021/jm050166g