4-((E)-4-((E)-4-hydroxystyryl)styryl)benzene-1,2-diol | 1256334-08-3

• 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: 4-((E)-4-((E)-4-hydroxystyryl)styryl)benzene-1,2-diol
• 英文别名: (E,E)-1-(4-hydroxystyryl)-4-(3,4-dihydroxystyryl)benzene；4-[(E)-2-[4-[(E)-2-(4-hydroxyphenyl)ethenyl]phenyl]ethenyl]benzene-1,2-diol
• CAS: 1256334-08-3
• 化学式: C₂₂H₁₈O₃
• 分子量: 330.383
• InChiKey: MDMSCZCYNMINHC-BSWSSELBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 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：

  3,4-二羟基苯甲醛 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 4-((E)-4-((E)-4-hydroxystyryl)styryl)benzene-1,2-diol
  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

• Hydroxylated di- and tri-styrylbenzenes, a new class of antiplasmodial agents: discovery and mechanism of action
  作者：Naina Sharma、Dinesh Mohanakrishnan、Amit Shard、Abhishek Sharma、Arun K. Sinha、Dinkar Sahal

  DOI：10.1039/c6ra06059e

  日期：——

  showed IC50 values of 0.9, 2.0 and 2.7 against 3D7 (chloroquine sensitive), Dd2 and Indo (chloroquine resistant) strains of Plasmodium falciparum respectively. Moreover, 27 and 11, which exhibited selectivity indices of 40 and >111 were also found to be nontoxic to the HeLa cell line. Microscopic studies revealed that the rings and trophozoites obtained from the 27 and 11 (an octupolar tristyrylbenzene

  首次系统评价了天然产物和二/三苯乙烯基苯的羟基二苯乙烯家族的抗疟原虫活性。使用修饰的Knoevenagel-Perkin-脱羧化-Heck序列，从容易获得的起始材料（即，羟基苯甲醛-苯乙酸-芳基卤化物）中快速合成了27个不同取代的羟基类苯乙烯类化合物的文库。评价了这些化合物对三种不同菌株恶性疟原虫的体外抗血浆活性。值得注意的是，4,4'4'' - （（1- Ë，1' ë，1'' Ë） -苯-1,3,5-三基三（乙烯-2,1-二基））三（2,6-二甲氧基苯酚）（27），一种八极类芪，对3D7（对氯喹敏感），Dd2和I​​ndo（对氯喹抗性）菌株的IC 50（μM）值分别为0.6、0.5和1.36，而二苯乙烯基苯（11）的IC 50值为0.9、2.0和2.7。的恶性疟原虫分别。此外，还发现选择性指数为40和> 111的27和11对HeLa细胞系无毒。显微镜研究表明，从27和11获得的环和滋养体
• 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.