(E,E)-1,3-bis(4-hydroxystyryl)benzene | 1202480-76-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (E,E)-1,3-bis(4-hydroxystyryl)benzene
• 英文别名: (E,E)-3,5-bis-(4'-hydroxystyryl)benzene；4-[(E)-2-[3-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl]ethenyl]phenol
• CAS: 1202480-76-9
• 化学式: C₂₂H₁₈O₂
• 分子量: 314.384
• InChiKey: LMAFIHWUCNBINV-YDFGWWAZSA-N

物化性质

• 熔点：
  218-220 °C (decomp)
• 沸点：
  522.4±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  24
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间二溴苄 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 (E,E)-1,3-bis(4-hydroxystyryl)benzene
  参考文献：
  名称：

  Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers

  摘要：

  Starting from bisphenolic bis-styrylbenzene DF-9 (4), P-amyloid (A beta) binding affinity and specificity for phenolic bis-styrylbenzenes, monostyrylbenzenes, and alkyne controls were determined by fluorescence titration with beta-amyloid peptide A beta(1-40) and a fluorescence assay using APP/PSI transgenic mouse brain sections. Bis-styrylbenzene SA R is derived largely from work on symmetrical compounds. This study is the first to describe A beta binding data for bis-styrylbenzenes unsymmetrical in the outer rings. With one exception, binding affinity and specificity were decreased by adding and/or changing the substitution pattern of phenol functional groups, changing the orientation about the central phenyl ring, replacing the alkene with alkyne bonds, or eliminating the central phenyl ring. The only compound with an A beta binding affinity and specificity comparable to 4 was its 3-hydroxy regioisomer 8. Like 4, 8 crossed the blood brain barrier and bound to A beta plaques in vivo. By use of a DPPH assay, phenol functional groups with papa orientations seem to be a necessary. but insufficient, criterion for good free radical scavenging properties in these compounds.

  DOI：

  10.1021/jm1006929

文献信息

• Small molecules that protect against β-amyloid-induced cytotoxicity by inhibiting aggregation of β-amyloid
  作者：Yun Suk Lee、Hye Yun Kim、YoungSoo Kim、Jae Hong Seo、Eun Joo Roh、Hogyu Han、Kye Jung Shin

  DOI：10.1016/j.bmc.2012.06.045

  日期：2012.8

  Aggregated beta-amyloid (A beta) plays crucial roles in Alzheimer's disease (AD) pathogenesis, therefore blockade of Ab aggregation is considered as a potential therapeutic target. We designed and synthesized small molecules to reduce A beta-induced cytotoxicity by inhibiting A beta aggregation. The small molecules were screened via ThT, MTT, and cell-based cytotoxicity assay (A beta burden assay). Selected compounds 1c, 1d, 1e, and 1f were then investigated by evaluating their effects on cognitive impairment of acute AD mice model. Learning and memory dysfunction by injection of A beta(1-42) was recovered by administration of these molecules. Especially, 1d showed the best recovery activity in Y-maze task, object recognition task, and passive avoidance task with dose dependent manner. These results suggest that 1d has high potential as a therapeutic agent for AD. (C) 2012 Elsevier Ltd. All rights reserved.
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  公开号：US20090326275A1

  公开（公告）日：2009-12-31

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• METHYLENE BLUE - CURCUMIN ANALOG FOR THE TREATMENT OF ALZHEIMER'S DISEASE
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  公开号：US20100190978A1

  公开（公告）日：2010-07-29

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  公开号：US20100286585A1

  公开（公告）日：2010-11-11

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  公开（公告）日：2010-11-18

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