(E,E)-1,4-bis(2-pyridylethenyl)benzene | 21899-23-0

• 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,E)-1,4-bis(2-pyridylethenyl)benzene
• 英文别名: 1,4-Bis-(2-vinylpyridyl)-benzene；1.4-Bis-(2-benzol；2,2'-(2,2'-p-phenylene-divinyl)-bis-pyridine；1,4-bis-(trans-2-[2]pyridyl-vinyl)-benzene；1,4-Bis-(trans-2-[2]pyridyl-vinyl)-benzol；1,4-Bis-(beta-pyridyl-2-vinyl)-benzene；2-[(E)-2-[4-[(E)-2-pyridin-2-ylethenyl]phenyl]ethenyl]pyridine
• CAS: 21899-23-0
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: WQOWWVOKDZZKCN-PHEQNACWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-二(溴甲基)苯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 32.33h， 生成 (E,E)-1,4-bis(2-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

• Blout; Eager, Journal of the American Chemical Society, 1945, vol. 67, p. 1315,1317
  作者：Blout、Eager

  DOI：——

  日期：——
• Synthesis, optical, and thermal properties of conjugated, bispyridyl and tetrapyridyl compounds by Knoevenagel reaction
  作者：Pradip K. Bhowmik、Alexi K. Nedeltchev、Haesook Han

  DOI：10.1016/j.tetlet.2007.06.019

  日期：2007.7

  A series of conjugated, bispyridyl and tetrapyridyl compounds were synthesized from either terephthalaldehyde or isophthalaldehyde and activated pyridyl compounds by Knoevenagel reaction on heating in acetic anhydride in presence of acetic acid and their optical and thermal properties were examined. All of them exhibited photoluminescence in chloroform, tetrahydrofuran, and dimethyl sulfoxide as well as in solid state. In solid state, their emission spectra exhibited bathochromic shifts when compared with those in less or more polar solvents. Some compounds emitted UV light both in polar solvents and in the solid state; other compounds emitted UV light in polar solvents, but emitted visible light in the solid state. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.