tert-butyl N-[5-(5-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-1-benzofuran-2-yl)pyridin-2-yl]-N-methylcarbamate | 1287783-05-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl N-[5-(5-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-1-benzofuran-2-yl)pyridin-2-yl]-N-methylcarbamate
• 英文别名: tert-butyl 5-(5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)-1-benzofuran-2-yl)-2-pyridinyl-N-methylcarbamate；tert-butyl N-[5-[5-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1-benzofuran-2-yl]pyridin-2-yl]-N-methylcarbamate
• CAS: 1287783-05-4
• 化学式: C₂₅H₃₂N₂O₇
• 分子量: 472.538
• InChiKey: CEDMPOWMSGFLBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[5-(5-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-1-benzofuran-2-yl)pyridin-2-yl]-N-methylcarbamate 在 盐酸 、 potassium carbonate 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.16h， 生成 5-(5-(2-(2-(2-(18)F-fluoroethoxy)ethoxy)ethoxy)benzofuran-2-yl)-N-methylpyridin-2-amine
  参考文献：
  名称：

  Novel ¹⁸F-Labeled Benzofuran Derivatives with Improved Properties for Positron Emission Tomography (PET) Imaging of β-Amyloid Plaques in Alzheimer’s Brains

  摘要：

  In vivo imaging of beta-amyloid plaques in the brain may lead to the early diagnosis of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of treatment. In the present study, we report on the development two potential PET probes, [F-18]FPYBF-2 ([F-18]10) and [F-18]FPHBF-2 ([F-18]21), for imaging of beta-amyloid plagues in AD brain. In experiments in vitro, 10 and 21 displayed high affinity for A beta(1-42) aggregates (K-i = 2.41 and 3.85 nM, respectively). In biodistribution experiments using normal mice, they displayed high uptake in the brain (7.38 and 8.18% ID/g at 2 mm postinjection,, respectively), and the radioactivity washed out from the, brain rapidly (3.15 and 3.87% ID/g at 60 min postinjection, respectively), which is highly desirable for beta-amyloid imaging agents. In vivo, they clearly labeled beta-amyloid plaques in Tg2576 mice. Furthermore, the specific labeling of beta-amyloid plaques by 10 and 21 was observed in autoradiographs of sections of autopsied AD brain. These new fluorinated benzofuran derivatives are promising PET probes for imaging cerebral beta-amyloid plaques.

  DOI：

  10.1021/jm200057u
• 作为产物：
  描述：

  5-甲氧基苯并呋喃-2-硼酸 在 咪唑 、 四(三苯基膦)钯 、 四丁基氟化铵 、 sodium methylate 、 三溴化硼 、 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 tert-butyl N-[5-(5-{2-[2-(2-hydroxyethoxy)ethoxy]ethoxy}-1-benzofuran-2-yl)pyridin-2-yl]-N-methylcarbamate
  参考文献：
  名称：

  JP5825608

  摘要：

  公开号：

文献信息

• JP5825608
  申请人：——

  公开号：——

  公开（公告）日：——
• Novel ¹⁸F-Labeled Benzofuran Derivatives with Improved Properties for Positron Emission Tomography (PET) Imaging of β-Amyloid Plaques in Alzheimer’s Brains
  作者：Masahiro Ono、Yan Cheng、Hiroyuki Kimura、Mengchao Cui、Shinya Kagawa、Ryuichi Nishii、Hideo Saji

  DOI：10.1021/jm200057u

  日期：2011.4.28

  In vivo imaging of beta-amyloid plaques in the brain may lead to the early diagnosis of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of treatment. In the present study, we report on the development two potential PET probes, [F-18]FPYBF-2 ([F-18]10) and [F-18]FPHBF-2 ([F-18]21), for imaging of beta-amyloid plagues in AD brain. In experiments in vitro, 10 and 21 displayed high affinity for A beta(1-42) aggregates (K-i = 2.41 and 3.85 nM, respectively). In biodistribution experiments using normal mice, they displayed high uptake in the brain (7.38 and 8.18% ID/g at 2 mm postinjection,, respectively), and the radioactivity washed out from the, brain rapidly (3.15 and 3.87% ID/g at 60 min postinjection, respectively), which is highly desirable for beta-amyloid imaging agents. In vivo, they clearly labeled beta-amyloid plaques in Tg2576 mice. Furthermore, the specific labeling of beta-amyloid plaques by 10 and 21 was observed in autoradiographs of sections of autopsied AD brain. These new fluorinated benzofuran derivatives are promising PET probes for imaging cerebral beta-amyloid plaques.