4-[6-(1,3-Benzothiazol-2-yl)-1,3-benzothiazol-2-yl]aniline | 909904-76-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 4-[6-(1,3-Benzothiazol-2-yl)-1,3-benzothiazol-2-yl]aniline
• CAS: 909904-76-3
• 化学式: C₂₀H₁₃N₃S₂
• 分子量: 359.475
• InChiKey: VVYFGERDCVGTGO-UHFFFAOYSA-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：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[6-(1,3-Benzothiazol-2-yl)-1,3-benzothiazol-2-yl]aniline 在 一氯化碘 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 以38%的产率得到4-[2,6']dibenzothiazolyl-20-yl-2-iodophenylamine
  参考文献：
  名称：

  AMYLOID-IMAGING AGENTS

  摘要：

  用于检测主体中淀粉样蛋白的分子探针包括二苯并噻唑衍生物。

  公开号：

  US20090123373A1
• 作为产物：
  描述：

  2-(4-nitrophenyl)benzothiazole-6-carbonyl chloride 在 盐酸 、 tin(ll) chloride 作用下， 以 乙醇 、 水 、 氯苯 为溶剂， 反应 4.0h， 生成 4-[6-(1,3-Benzothiazol-2-yl)-1,3-benzothiazol-2-yl]aniline
  参考文献：
  名称：

  Dibenzothiazoles as novel amyloid-imaging agents

  摘要：

  Novel dibenzothiazole derivatives were synthesized and evaluated as amyloid-imaging agents. In vitro quantitative binding studies using AD brain tissue homogenates showed that the dibenzothiazole derivatives displayed high binding affinities with K-i values in the nanomolar range (6.8-36 nM). These derivatives are relatively lipophilic with partition coefficients (logP oct) in the range of 1.25-3.05. Preliminary structure-activity relationship studies indicated dibenzothiazole derivatives bearing electron-donating groups exhibited higher binding affinities than those bearing electron-withdrawing groups. A lead compound was selected for its high binding affinity and radiolabeled with [I-125] through direct radioiodination using sodium [I-125] iodide in the presence of Chloramine T. The radioligand (4-[2,6']dibenzothiazolyl-2'-yl-2-[I-125]-phenylamine) displayed moderate lipophilicity (logP oct, 2.70), very good brain uptake (3.71 +/- 0.63% ID/g at 2 min after iv injection in mice), and rapid washout from normal brains (0.78% and 0.43% ID/g at 30 and 60 min, respectively). These studies indicated that lipophilic dibenzothiazole derivatives represent a promising pharmacophore for the development of novel amyloid-imaging agents for potential application in Alzheimer's disease and related neurodegenerative disorders. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.11.022

文献信息

• AMYLOID-IMAGING AGENTS
  申请人：WANG YANMING

  公开号：US20090123373A1

  公开（公告）日：2009-05-14

  A molecular probe for use in the detection of amyloid in a subject includes a dibenzothiazole derivative.

  用于检测主体中淀粉样蛋白的分子探针包括二苯并噻唑衍生物。
• Dibenzothiazoles as novel amyloid-imaging agents
  作者：Chunying Wu、Jingjun Wei、Kuanqiang Gao、Yanming Wang

  DOI：10.1016/j.bmc.2006.11.022

  日期：2007.4

  Novel dibenzothiazole derivatives were synthesized and evaluated as amyloid-imaging agents. In vitro quantitative binding studies using AD brain tissue homogenates showed that the dibenzothiazole derivatives displayed high binding affinities with K-i values in the nanomolar range (6.8-36 nM). These derivatives are relatively lipophilic with partition coefficients (logP oct) in the range of 1.25-3.05. Preliminary structure-activity relationship studies indicated dibenzothiazole derivatives bearing electron-donating groups exhibited higher binding affinities than those bearing electron-withdrawing groups. A lead compound was selected for its high binding affinity and radiolabeled with [I-125] through direct radioiodination using sodium [I-125] iodide in the presence of Chloramine T. The radioligand (4-[2,6']dibenzothiazolyl-2'-yl-2-[I-125]-phenylamine) displayed moderate lipophilicity (logP oct, 2.70), very good brain uptake (3.71 +/- 0.63% ID/g at 2 min after iv injection in mice), and rapid washout from normal brains (0.78% and 0.43% ID/g at 30 and 60 min, respectively). These studies indicated that lipophilic dibenzothiazole derivatives represent a promising pharmacophore for the development of novel amyloid-imaging agents for potential application in Alzheimer's disease and related neurodegenerative disorders. (c) 2007 Elsevier Ltd. All rights reserved.