3-<4'-(2''-(3'''-pyridyl)vinyl)-α-styryl>pyridin | 29820-77-7

• 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: 3-<4'-(2''-(3'''-pyridyl)vinyl)-α-styryl>pyridin
• 英文别名: 1,4-Bis<β-pyridyl-(2)-vinyl>benzene；(E,E)-1,4-bis(3-pyridylethenyl)benzene；3,3'-(2,2'-p-phenylene-divinyl)-bis-pyridine；1,4-Bis--benzol；1,4-Bis(3-pyridyl-2-vinyl)benzene；3-[(E)-2-[4-[(E)-2-pyridin-3-ylethenyl]phenyl]ethenyl]pyridine
• CAS: 29820-77-7
• 化学式: C₂₀H₁₆N₂
• 分子量: 284.36
• InChiKey: KVIZESINYFLTIT-WGDLNXRISA-N

物化性质

• 沸点：
  469.4±40.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  对二甲苯 在 sodium bromate 、 potassium tert-butylate 、 sodium hydrogensulfite 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 37.33h， 生成 3-<4'-(2''-(3'''-pyridyl)vinyl)-α-styryl>pyridin
  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

• Anil-Synthese 22. Mitteilung über die Herstellung von Styryl-und Distyryl-Derivaten des Pyridins
  作者：Adolf Emil Siegrist、Hans Rudolf Meyer、Peter Gassmann、Serge Moss

  DOI：10.1002/hlca.19800630524

  日期：1980.7.9

  Preparation of Styryl and Distyryl Derivatives of Pyridine

  吡啶的苯乙烯基和二苯乙烯基衍生物的制备
• SIEGRIST A. E.; MEYER H. R.; GASSMANN P.; MOSS S., HELV. CHIM. ACTA, 1980, 63, NO 5, 1311-1334
  作者：SIEGRIST A. E.、 MEYER H. R.、 GASSMANN P.、 MOSS S.

  DOI：——

  日期：——
• 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.

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