4-amino-4'-(1-fluoro-3-hydroxypropane-2-ylmethoxy)stilbene | 902143-12-8

• 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-amino-4'-(1-fluoro-3-hydroxypropane-2-ylmethoxy)stilbene
• 英文别名: 3-{4-[(E)-2-(4-Amino-phenyl)-vinyl]-phenoxy}-2-fluoromethyl-propan-1-ol；2-[[4-[(E)-2-(4-aminophenyl)ethenyl]phenoxy]methyl]-3-fluoropropan-1-ol
• CAS: 902143-12-8
• 化学式: C₁₈H₂₀FNO₂
• 分子量: 301.361
• InChiKey: KGYLKTLZDMCQTM-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-amino-4'-(1-fluoro-3-hydroxypropane-2-ylmethoxy)stilbene 、 聚合甲醛 在 sodium methylate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到4-N-methylamino-4'-(1-fluoro-3-hydroxypropane-2-ylmethoxy)stilbene
  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：

  toluene-4-sulfonic acid 2-hydroxymethyl-3-{4-[2-(4-nitrophenyl)vinyl]phenoxy}propyl ester 在 盐酸 、 四丁基氟化铵 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 4-amino-4'-(1-fluoro-3-hydroxypropane-2-ylmethoxy)stilbene
  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

文献信息

• Stilbene derivatives and their use for binding and imaging amyoid plaques
  申请人：Kung F. Hank

  公开号：US20060269473A1

  公开（公告）日：2006-11-30

  This invention relates to a method of imaging amyloid deposits and to labeled compounds, and methods of making labeled compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.

  本发明涉及成像淀粉样沉积物的方法以及标记化合物，以及制备用于成像淀粉样沉积物的标记化合物的方法。本发明还涉及化合物以及制备化合物的方法，用于抑制淀粉样蛋白聚集形成淀粉样沉积物，并将治疗剂输送到淀粉样沉积物。
• Stilbene derivatives and their use for binding and imaging amyloid plaques
  申请人：Kung F. Hank

  公开号：US20060269474A1

  公开（公告）日：2006-11-30

  This invention relates to a method of imaging amyloid deposits and to labeled compounds, and methods of making labeled compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.

  本发明涉及一种成像淀粉样沉积物的方法，以及标记化合物和制备标记化合物的方法，以用于成像淀粉样沉积物。此外，本发明还涉及化合物和制备化合物的方法，以抑制淀粉样蛋白聚集形成淀粉样沉积物，并将治疗剂递送到淀粉样沉积物的方法。
• STILBENE DERIVATIVES AND THEIR USE FOR BINDING AND IMAGING AMYLOID PLAQUES
  申请人：Kung Hank F.

  公开号：US20100266500A1

  公开（公告）日：2010-10-21

  This invention relates to a method of imaging amyloid deposits and to labeled compounds, and methods of making labeled compounds useful in imaging amyloid deposits. This invention also relates to compounds, and methods of making compounds for inhibiting the aggregation of amyloid proteins to form amyloid deposits, and a method of delivering a therapeutic agent to amyloid deposits.

  本发明涉及一种成像淀粉样沉积物的方法，以及标记化合物和制备标记化合物的方法，以便成像淀粉样沉积物。本发明还涉及化合物，以及制备化合物的方法，用于抑制淀粉样蛋白聚集形成淀粉样沉积物，并且涉及将治疗剂输送到淀粉样沉积物的方法。
• WO2006/66104
  申请人：——

  公开号：——

  公开（公告）日：——
• US7807135B2
  申请人：——

  公开号：US7807135B2

  公开（公告）日：2010-10-05