(E,E)-1-methoxy-2,5-bis(3-pyridylethenyl)benzene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E,E)-1-methoxy-2,5-bis(3-pyridylethenyl)benzene
• 英文别名: 3-[(E)-2-[2-methoxy-4-[(E)-2-pyridin-3-ylethenyl]phenyl]ethenyl]pyridine
• 化学式: C₂₁H₁₈N₂O
• 分子量: 314.387
• InChiKey: YVVKAXHGTSHBOG-RXUIJTJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,4-bis(bromomethyl)-2-methoxybenzene 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 32.33h， 生成 (E,E)-1-methoxy-2,5-bis(3-pyridylethenyl)benzene
  参考文献：
  名称：

  Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds

  摘要：

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential A beta imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower LogP values, and studied their fluorescent properties and A beta binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for A beta plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a LogP value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl) benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents. (C) 2016 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2016.05.022

文献信息

• Bis-pyridylethenyl benzene as novel backbone for amyloid-β binding compounds
  作者：Rob J.A. Nabuurs、Varsha V. Kapoerchan、Athanasios Metaxas、Sarah Hafith、Maaike de Backer、Mick M. Welling、Wim Jiskoot、Adrianus M.C.H. van den Nieuwendijk、Albert D. Windhorst、Herman S. Overkleeft、Mark A. van Buchem、Mark Overhand、Louise van der Weerd

  DOI：10.1016/j.bmc.2016.05.022

  日期：2016.12

  Detection of cerebral beta-amyloid (A beta) by targeted contrast agents is of great interest for in vivo diagnosis of Alzheimer's disease (AD). Partly because of their planar structure several bis-styrylbenzenes have been previously reported as potential A beta imaging agents. However, these compounds are relatively hydrophobic, which likely limits their in vivo potential. Based on their structures, we hypothesized that less hydrophobic bis-pyridylethenylbenzenes may also label amyloid. We synthesized several bis-pyridylethenylbenzenes and tested whether these compounds indeed display improved solubility and lower LogP values, and studied their fluorescent properties and A beta binding characteristics. Bis-pyridylethenylbenzenes showed a clear affinity for A beta plaques on both human and murine AD brain sections. Competitive binding experiments suggested a different binding site than Chrysamine G, a well-known stain for amyloid. With a LogP value between 3 and 5, most bis-pyridylethenylbenzenes were able to enter the brain and label murine amyloid in vivo with the bis(4-pyridylethenyl) benzenes showing the most favorable characteristics. In conclusion, the presented results suggest that bis-pyridylethenylbenzene may serve as a novel backbone for amyloid imaging agents. (C) 2016 Published by Elsevier Ltd.