tert-butyl N-(4-(5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzo[d]-oxazol-2-yl)phenyl)-N-(methyl)carbamate | 1383563-15-2

• 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: tert-butyl N-(4-(5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzo[d]-oxazol-2-yl)phenyl)-N-(methyl)carbamate
• 英文别名: tert-butyl N-[4-[5-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]-1,3-benzoxazol-2-yl]phenyl]-N-methylcarbamate
• CAS: 1383563-15-2
• 化学式: C₂₅H₃₂N₂O₇
• 分子量: 472.538
• InChiKey: WZEWMMMIZQBTEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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-(4-(5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzo[d]-oxazol-2-yl)phenyl)-N-(methyl)carbamate 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以52.4%的产率得到2-(2-(2-((2-N-(4-((tert-butoxycarbonyl)-N-(methyl)amino)phenyl)-benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethyl methanesulfonate
  参考文献：
  名称：

  Novel ¹⁸F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo-[d]oxazol-2-yl)-N-methylaniline ([F-18]24) and 4-(5-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([F-18]32), were synthesized and evaluated as probes for imaging cerebral beta-amyloid (A beta) plaques in living brain tissue by PET. [F-18]24 and [F-18]32 displayed high affinity for A beta(1-42) aggregates (K-1 = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [F-18]24 also displayed excellent binding to A beta plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [F-18]24 between Tg2576 and wild-type mice. The results suggest [F-18]24 to be a useful PET agent for detecting A beta plaques in the living human brain.

  DOI：

  10.1021/jm300251n
• 作为产物：
  描述：

  4-甲氧基-2-硝基酚 在 咪唑 、 palladium 10% on activated carbon 、 四丁基氟化铵 、 氢气 、 三溴化硼 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 94.5h， 生成 tert-butyl N-(4-(5-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)benzo[d]-oxazol-2-yl)phenyl)-N-(methyl)carbamate
  参考文献：
  名称：

  Novel ¹⁸F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer’s Disease

  摘要：

  Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo-[d]oxazol-2-yl)-N-methylaniline ([F-18]24) and 4-(5-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([F-18]32), were synthesized and evaluated as probes for imaging cerebral beta-amyloid (A beta) plaques in living brain tissue by PET. [F-18]24 and [F-18]32 displayed high affinity for A beta(1-42) aggregates (K-1 = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [F-18]24 also displayed excellent binding to A beta plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [F-18]24 between Tg2576 and wild-type mice. The results suggest [F-18]24 to be a useful PET agent for detecting A beta plaques in the living human brain.

  DOI：

  10.1021/jm300251n

文献信息

• Novel ¹⁸F-Labeled Benzoxazole Derivatives as Potential Positron Emission Tomography Probes for Imaging of Cerebral β-Amyloid Plaques in Alzheimer’s Disease
  作者：Mengchao Cui、Masahiro Ono、Hiroyuki Kimura、Masashi Ueda、Yuji Nakamoto、Kaori Togashi、Yoko Okamoto、Masafumi Ihara、Ryosuke Takahashi、Boli Liu、Hideo Saji

  DOI：10.1021/jm300251n

  日期：2012.11.8

  Two radiofluoro-pegylated phenylbenzoxazole derivatives, 4-(5-(2-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo-[d]oxazol-2-yl)-N-methylaniline ([F-18]24) and 4-(5-(2-(2-[F-18]fluoroethoxy)ethoxy)ethoxy)benzo[d]oxazol-2-yl)-N,N-dimethylaniline ([F-18]32), were synthesized and evaluated as probes for imaging cerebral beta-amyloid (A beta) plaques in living brain tissue by PET. [F-18]24 and [F-18]32 displayed high affinity for A beta(1-42) aggregates (K-1 = 9.3 and 3.9 nM, respectively). In vitro autoradiography with sections of post-mortem AD brain and transgenic mouse brain confirmed the affinity of these tracers. Initial high uptake into and rapid washout from the brain in normal mice were observed. [F-18]24 also displayed excellent binding to A beta plaques in ex vivo autoradiographic experiments with Tg2576 mice. Furthermore, small-animal PET studies demonstrated significant differences in the clearance profile after the administration of [F-18]24 between Tg2576 and wild-type mice. The results suggest [F-18]24 to be a useful PET agent for detecting A beta plaques in the living human brain.