4-(5-methoxybenzo[d]oxazol-2-yl)-N,N-dimethylaniline | 1383563-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-methoxybenzo[d]oxazol-2-yl)-N,N-dimethylaniline
• 英文别名: 4-(5-methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylaniline
• CAS: 1383563-17-4
• 化学式: C₁₆H₁₆N₂O₂
• 分子量: 268.315
• InChiKey: BIZFSZYEKCGRJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-methoxybenzo[d]oxazol-2-yl)-N,N-dimethylaniline 在 三溴化硼 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 2-(2-(2-((2-(4-(dimethylamino)phenyl)benzo[d]oxazol-5-yl)oxy)ethoxy)ethoxy)ethanol
  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 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 24.5h， 生成 4-(5-methoxybenzo[d]oxazol-2-yl)-N,N-dimethylaniline
  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

• Design, synthesis, and applications of nucleic acid-specific benzoxazole-N,N-dialkylphenylamines derivatives for nucleolus imaging in the cells
  作者：Burak Kuzu、Eda Acikgoz、Mustafa Cakir

  DOI：10.1016/j.molstruc.2024.138199

  日期：2024.8

  the cells were examined under inverted and light microscopes, respectively, and the fluorescence potentials of selected compounds were determined using immunofluorescence microscopy. The fluorescence intensity of molecules and 3D interactive surface plot images of cells were analyzed using ImageJ software. Cell imaging analyses showed that BX-6 and BX-13, like ThT, specifically stain the cell nucleolus

  核仁被认为是大脑的核，其结构和功能的改变与许多细胞功能有关，因此会导致多种疾病。通过新型生物标志物鉴定核仁形态和活性，为开发多种人类疾病（包括癌症、神经退行性疾病和衰老）的治疗方法提供了新途径。因此，用荧光探针特异性检测核仁对于临床应用至关重要。本研究基于苯并噻唑类荧光探针硫磺素T（ThT），设计并合成了一系列苯并恶唑-二烷基苯胺衍生化合物。其中，苯并恶唑环上带有吸电子取代基的BX-3和BX-16分别在470和465 nM波长处具有较高的荧光发射。分别在倒置显微镜和光学显微镜下检查细胞的一般形态和分裂，并使用免疫荧光显微镜测定所选化合物的荧光电位。使用 ImageJ 软件分析分子的荧光强度和细胞的 3D 交互式表面图图像。细胞成像分析表明，BX-6 和 BX-13 与 ThT 一样，可以特异性地对细胞核仁进行染色。此外，分子对接研究表明，这些化合物可以通过与 RNA 结构中的鸟嘌呤区域高亲和力结合来识别富含
• Synthesis and biological evaluation of novel technetium-99m labeled phenylbenzoxazole derivatives as potential imaging probes for β-amyloid plaques in brain
  作者：Xuedan Wang、Mengchao Cui、Pingrong Yu、Zijing Li、Yanping Yang、Hongmei Jia、Boli Liu

  DOI：10.1016/j.bmcl.2012.05.010

  日期：2012.7

  Two uncharged Tc-99m-labeled phenylbenzoxazole derivatives were biologically evaluated as potential imaging probes for beta-amyloid plaques. The Tc-99m and corresponding rhenium complexes were synthesized by coupling monoamine-monoamide dithiol (MAMA) and bis(aminoethanethiol) (BAT) chelating ligand via a pentyloxy spacer to phenylbenzoxazole. The fluorescent rhenium complexes 6 and 9 selectively stainined the beta-amyloid plaques on the sections of transgenic mouse, and showed high affinity for A beta((1-42)) aggregates (K-i = 11.1 nM and 14.3 nM, respectively). Autoradiography in vitro indicated that [Tc-99m]6 clearly labeled beta-amyloid plaques on the sections of transgenic mouse. Biodistribution experiments in normal mice revealed that [Tc-99m]6 displayed moderate initial brain uptake (0.81% ID/g at 2 min), and quickly washed out from the brain (0.25% ID/g at 60 min). The preliminary results indicate that the properties of [Tc-99m]6 are promising, although additional refinements are needed to improve the ability to cross the blood-brain barrier. (C) 2012 Elsevier Ltd. All rights reserved.
• 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.