2-(2,2'-bithiophen-5-yl)-6-bromobenzo[d]thiazole | 1227867-91-5

• 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: 2-(2,2'-bithiophen-5-yl)-6-bromobenzo[d]thiazole
• 英文别名: 6-Bromo-2-(5-thiophen-2-ylthiophen-2-yl)-1,3-benzothiazole
• CAS: 1227867-91-5
• 化学式: C₁₅H₈BrNS₃
• 分子量: 378.337
• InChiKey: UULUHIZTWKCREF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-联噻吩-5-乙醛 、 2-氨基-5-溴苯硫醇 以 二甲基亚砜 为溶剂， 反应 0.42h， 以66.3%的产率得到2-(2,2'-bithiophen-5-yl)-6-bromobenzo[d]thiazole
  参考文献：
  名称：

  Synthesis and evaluation of novel benzothiazole derivatives based on the bithiophene structure as potential radiotracers for β-amyloid plaques in Alzheimer’s disease

  摘要：

  In this study, six novel benzothiazole derivatives based on the bithiophene structure were developed as potential beta-amyloid probes. In vitro binding studies using A beta aggregates showed that all of them demonstrated high binding affinities with K-i values ranged from 0.11 to 4.64 nM. In vitro fluorescent staining results showed that these compounds can intensely stained A beta plaques within brain sections of APP/PS1 transgenic mice, animal model for AD. Two radioiodinated compounds [I-125]-2-(5'-iodo-2,2'-bithiophen-5-yl)-6-methoxybenzo[d]thiazole [I-125]10 and [I-125]-2-(2,2'-bithiophen-5-yl)-6-iodobenzo[d]thiazole [I-125]13 were successfully prepared through an iododestannylation reaction. Furthermore, in vitro autoradiography of the AD model mice brain sections showed that both [I-125]10 and [I-125]13 labeled the A beta plaques specifically with low background. In vivo biodistribution studies in normal mice indicated that [I-125]13 exhibited high brain uptake (3.42% ID/g at 2 min) and rapid clearance from the brain (0.53% ID/g at 60 min), while [I-125]10 showed lower brain uptake (0.87% ID/g at 2 min). In conclusion, these preliminary results of this study suggest that the novel radioiodinated benzothiazole derivative [I-125]13 may be a candidate as an in vivo imaging agent for detecting beta-amyloid plaques in the brain of AD patients. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.002