(E,E)-1-(4-hydroxystyryl)-4-(3,5-dihydroxystyryl)benzene | 1256334-09-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E,E)-1-(4-hydroxystyryl)-4-(3,5-dihydroxystyryl)benzene
• 英文别名: 5-[(E)-2-[4-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl]ethenyl]benzene-1,3-diol
• CAS: 1256334-09-4
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: MMWRMJAZPFUPMP-BSWSSELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 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：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 在 盐酸 、 sodium methylate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (E,E)-1-(4-hydroxystyryl)-4-(3,5-dihydroxystyryl)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

• Phenolic Bis-styrylbenzenes as β-Amyloid Binding Ligands and Free Radical Scavengers
  作者：Daniel P. Flaherty、Tomomi Kiyota、Yuxiang Dong、Tsuneya Ikezu、Jonathan L. Vennerstrom

  DOI：10.1021/jm1006929

  日期：2010.11.25

  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.