2-((1E,3E)-4-(6-([¹¹C]methylamino)pyridine-3-yl)buta-1,3-dienyl)benz[d]thiazole-6-ol | 1565797-40-1

• 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: 2-((1E,3E)-4-(6-([¹¹C]methylamino)pyridine-3-yl)buta-1,3-dienyl)benz[d]thiazole-6-ol
• 英文别名: 2-((1E,3E)-4-(6-[¹¹C]methylaminopyridin-3-yl)buta-1,3-dien-1-yl)benzo[d]thiazol-6-ol；(5-((1E,3E)-4-(6-[(11)C]methylamino)pyridin-3-yl)buta-1,3-dien-1-yl)benzo[d]thiazol-6-ol；(11)C-PBB3；6-Benzothiazolol, 2-((1E,3E)-4-(6-(methyl-11c-amino)-3-pyridinyl)-1,3-butadien-1-yl)-；2-[(1E,3E)-4-[6-((111C)methylamino)pyridin-3-yl]buta-1,3-dienyl]-1,3-benzothiazol-6-ol
• CAS: 1565797-40-1
• 化学式: C₁₇H₁₅N₃OS
• 分子量: 308.381
• InChiKey: LBCRWMJTAFCLCL-DXDJJUBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  86.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 水 作用下， 以 二甲基亚砜 为溶剂， 反应 0.05h， 生成 2-((1E,3E)-4-(6-([¹¹C]methylamino)pyridine-3-yl)buta-1,3-dienyl)benz[d]thiazole-6-ol
  参考文献：
  名称：

  Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer’s disease

  摘要：

  The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [C-11]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with SPE in 20-25% and 15-20% radiochemical yield, respectively, based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was > 99%, and the specific activity at EOB was 370-1110 GBq/mu mol with a total synthesis time of similar to 40-min from EOB. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.08.053

文献信息

• Novel Compounds for Imaging Tau Proteins That Accumulate In Brain
  申请人：National Institute of Radiological Sciences

  公开号：US20150239878A1

  公开（公告）日：2015-08-27

  The present invention provides a compound represented by the following formula (I), a pharmaceutically acceptable salt thereof, or a solvate thereof. wherein: R 1 and R 2 are each separately selected from the group consisting of hydrogen, alkyl, alkenyl, acyl, and hydroxyalkyl; R 3 is hydrogen or halogen; ring A is a benzene ring or a pyridine ring; ring B is selected from the group consisting of the following formulas (i), (ii), (iii), and (iv): in the formula (ii), R a is alkyl; R 4 and R 5 are each separately selected from the group consisting of hydrogen, hydroxy, alkoxy, haloalkoxy, halohydroxyalkoxy, and aminoalkyl; and [Formula 3] represents a double bond or a triple bond. The above compound can be used as a molecular probe for imaging tau proteins that accumulate in the brain.

  本发明提供了一种化合物，其表示为以下式子（I），其药学上可接受的盐或其溶剂化物。其中：R1和R2各自独立地选择自氢，烷基，烯基，酰基和羟基烷基的群组；R3是氢或卤素；环A是苯环或吡啶环；环B选择自以下式子（i），（ii），（iii）和（iv）的群组：在式子（ii）中，Ra是烷基；R4和R5各自独立地选择自氢，羟基，烷氧基，卤代烷氧基，卤代羟基烷氧基和氨基烷基的群组；以及[公式3]表示双键或三键。以上化合物可用作成像在脑中积累的tau蛋白的分子探针。
• NOVEL COMPOUND FOR IMAGING TAU PROTEIN ACCUMULATED IN THE BRAIN
  申请人：National Institutes for Quantum and Radiological Science and Technology

  公开号：EP2767532B1

  公开（公告）日：2016-07-13
• Synthesis of a PET tau tracer [11C]PBB3 for imaging of Alzheimer’s disease
  作者：Min Wang、Mingzhang Gao、Zhidong Xu、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2015.08.053

  日期：2015.10

  The authentic standard PBB3 and its precursor N-desmethyl-PBB3 as well as TBS-protected N-desmethyl-PBB3 precursor for radiolabeling were synthesized from 5-bromo-2-nitropyridine, acrolein diethyl acetal, 6-methoxy-2-methylbenzothiazole, and diethylchlorophosphate with overall chemical yield 1% in six steps, 2% in five steps, and 1% in six steps, respectively. [C-11]PBB3 was prepared from either desmethyl-PBB3 or TBS-protected desmethyl-PBB3 with [C-11]CH3OTf through N-[C-11] methylation and isolated by HPLC combined with SPE in 20-25% and 15-20% radiochemical yield, respectively, based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The radiochemical purity was > 99%, and the specific activity at EOB was 370-1110 GBq/mu mol with a total synthesis time of similar to 40-min from EOB. (C) 2015 Elsevier Ltd. All rights reserved.