(E)-5-bromo-5'-(4-tert-butylstyryl)-2,2'-bithiophene | 1207108-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: (E)-5-bromo-5'-(4-tert-butylstyryl)-2,2'-bithiophene
• 英文别名: 2-bromo-5-[5-[(E)-2-(4-tert-butylphenyl)ethenyl]thiophen-2-yl]thiophene
• CAS: 1207108-01-7
• 化学式: C₂₀H₁₉BrS₂
• 分子量: 403.407
• InChiKey: HBVLZUNQVJZELT-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 在 溴 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 (E)-5-bromo-5'-(4-tert-butylstyryl)-2,2'-bithiophene
  参考文献：
  名称：

  Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques

  摘要：

  In continuation of our investigation on the bithiophene structure as potential beta-amyloid probes, a series of (E)-5-styryl-2,2'-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to A beta(1-42) aggregates (K(i) = 0.10-41.05 nM). Moreover, two radio-iodinated probes, [(125)I]-(E)-5-(4-iodostyryl)-2,2'-bithiophene ([(125)I]8) and [(125)I]-(E)-5-iodo-5'-(4-methoxystyryl)-2,2'-bithiophene ([(125)I]31) were prepared. Both of them displayed specific labeling of A beta plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [(125)I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel beta-amyloid imaging probes. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.015

文献信息

• Novel (E)-5-styryl-2,2′-bithiophene derivatives as ligands for β-amyloid plaques
  作者：Mengchao Cui、Zijing Li、Ruikun Tang、Hongmei Jia、Boli Liu

  DOI：10.1016/j.ejmech.2011.04.015

  日期：2011.7

  In continuation of our investigation on the bithiophene structure as potential beta-amyloid probes, a series of (E)-5-styryl-2,2'-bithiophene (SBTP) derivatives was designed and synthesized. In vitro binding showed that all of them displayed high binding affinities to A beta(1-42) aggregates (K(i) = 0.10-41.05 nM). Moreover, two radio-iodinated probes, [(125)I]-(E)-5-(4-iodostyryl)-2,2'-bithiophene ([(125)I]8) and [(125)I]-(E)-5-iodo-5'-(4-methoxystyryl)-2,2'-bithiophene ([(125)I]31) were prepared. Both of them displayed specific labeling of A beta plaques in the brain sections of AD model mice with low background. In vivo biodistribution in normal mice indicated that [(125)I]8 exhibited high initial brain uptake (2.11% ID/g at 2 min) and rapid clearance (0.41% ID/g at 30 min). These preliminary results suggest that SBTP derivatives may be served as novel beta-amyloid imaging probes. (C) 2011 Elsevier Masson SAS. All rights reserved.