(E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate | 1346502-40-6

• 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: (E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
• 英文别名: 2-[2-[2-[2-[5-[(E)-2-[4-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]phenyl]ethenyl]pyridin-2-yl]oxyethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
• CAS: 1346502-40-6
• 化学式: C₃₄H₄₄N₂O₉S
• 分子量: 656.797
• InChiKey: CMPHBBRTPJAKII-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  46
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate 在 4-二甲氨基吡啶 、 sodium azide 、 四丁基氟化铵 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 N,N-bis(2-(((E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethyl)amino)-2-oxoethyl)-2-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)acetamide
  参考文献：
  名称：

  Multidentate ¹⁸F-Polypegylated Styrylpyridines As Imaging Agents for Aβ Plaques in Cerebral Amyloid Angiopathy (CAA)

  摘要：

  beta-Amyloid plaques (A beta plaques) in the brain are associated with cerebral amyloid angiopathy (CAA). Imaging agents that could target the A beta plaques in the living human brain would be potentially valuable as biomarkers in patients with CAA. A new series of F-18 styrylpyridine derivatives with high molecular weights for selectively targeting A beta plaques in the blood vessels of the brain but excluded from the brain parenchyma is reported. The styrylpyridine derivatives, 8a-c, display high binding affinities and specificity to A beta plaques (K-i = 2.87, 3.24, and 7.71 nM, respectively). In vitro autoradiography of [F-18]8a shows labeling of beta-amyloid plaques associated with blood vessel walls in human brain sections of subjects with CAA and also in the tissue of AD brain sections. The results suggest that [F-18]8a may be a useful PET imaging agent for selectively detecting A beta plaques associated with cerebral vessels in the living human brain.

  DOI：

  10.1021/jm2009106
• 作为产物：
  描述：

  4-乙烯苯胺 在 4-二甲氨基吡啶 、 四丁基溴化铵 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.83h， 生成 (E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  Multidentate ¹⁸F-Polypegylated Styrylpyridines As Imaging Agents for Aβ Plaques in Cerebral Amyloid Angiopathy (CAA)

  摘要：

  beta-Amyloid plaques (A beta plaques) in the brain are associated with cerebral amyloid angiopathy (CAA). Imaging agents that could target the A beta plaques in the living human brain would be potentially valuable as biomarkers in patients with CAA. A new series of F-18 styrylpyridine derivatives with high molecular weights for selectively targeting A beta plaques in the blood vessels of the brain but excluded from the brain parenchyma is reported. The styrylpyridine derivatives, 8a-c, display high binding affinities and specificity to A beta plaques (K-i = 2.87, 3.24, and 7.71 nM, respectively). In vitro autoradiography of [F-18]8a shows labeling of beta-amyloid plaques associated with blood vessel walls in human brain sections of subjects with CAA and also in the tissue of AD brain sections. The results suggest that [F-18]8a may be a useful PET imaging agent for selectively detecting A beta plaques associated with cerebral vessels in the living human brain.

  DOI：

  10.1021/jm2009106

文献信息

• ⁶⁸Ga-Bivalent Polypegylated Styrylpyridine Conjugates for Imaging Aβ Plaques in Cerebral Amyloid Angiopathy
  作者：Zhihao Zha、Jin Song、Seok Rye Choi、Zehui Wu、Karl Ploessl、Megan Smith、Hank Kung

  DOI：10.1021/acs.bioconjchem.6b00127

  日期：2016.5.18

  (CAA). In an effort to selectively map these Aβ plaques, we are reporting a new series of 68Ga labeled styrylpyridine derivatives with high molecular weights. In vitro binding to Aβ plaques in post-mortem Alzheimer’s disease (AD) brain tissue showed that these 68Ga labeled bivalent styrylpyridines displayed good affinities and specificity (Ki < 30 nM). In vitro autoradiography using post-mortem AD brain

  沉积在血管上的Aβ斑块与脑淀粉样血管病（CAA）相关。为了选择性地定位这些Aβ斑块，我们报告了一系列新的68 Ga标记的高分子量苯乙烯基吡啶衍生物。死后阿尔茨海默氏病（AD）脑组织中Aβ斑块的体外结合表明，这些68 Ga标记的二价苯乙烯基吡啶具有良好的亲和力和特异性（K i <30 nM）。使用验尸AD脑切片的体外放射自显影显示了这68种物质的特异性结合Ga复合物与Aβ斑块。在正常小鼠中进行的生物分布研究表明，初始大脑的摄取量非常低（<0.3％剂量/ g），表明血脑屏障（BBB）渗透率很低。初步结果表明，68 Ga标记的二价苯乙烯基吡啶可能是有前途的候选物，作为检测CAA的PET成像放射性示踪剂。
• Multidentate ¹⁸F-Polypegylated Styrylpyridines As Imaging Agents for Aβ Plaques in Cerebral Amyloid Angiopathy (CAA)
  作者：Zhihao Zha、Seok Rye Choi、Karl Ploessl、Brian P. Lieberman、Wenchao Qu、Franz Hefti、Mark Mintun、Daniel Skovronsky、Hank F. Kung

  DOI：10.1021/jm2009106

  日期：2011.12.8

  beta-Amyloid plaques (A beta plaques) in the brain are associated with cerebral amyloid angiopathy (CAA). Imaging agents that could target the A beta plaques in the living human brain would be potentially valuable as biomarkers in patients with CAA. A new series of F-18 styrylpyridine derivatives with high molecular weights for selectively targeting A beta plaques in the blood vessels of the brain but excluded from the brain parenchyma is reported. The styrylpyridine derivatives, 8a-c, display high binding affinities and specificity to A beta plaques (K-i = 2.87, 3.24, and 7.71 nM, respectively). In vitro autoradiography of [F-18]8a shows labeling of beta-amyloid plaques associated with blood vessel walls in human brain sections of subjects with CAA and also in the tissue of AD brain sections. The results suggest that [F-18]8a may be a useful PET imaging agent for selectively detecting A beta plaques associated with cerebral vessels in the living human brain.