[11C-carbonyl] AR-A014418 | 1365994-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: [11C-carbonyl] AR-A014418
• CAS: 1365994-39-3
• 化学式: C₁₂H₁₂N₄O₄S
• 分子量: 307.307
• InChiKey: YAEMHJKFIIIULI-KXMUYVCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  106.39
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-氨基-5-硝基噻唑 、 以 二甲基亚砜 、 乙腈 为溶剂， 反应 0.02h， 生成 [11C-carbonyl] AR-A014418
  参考文献：
  名称：

  Towards the preparation of radiolabeled 1-aryl-3-benzyl ureas: Radiosynthesis of [11C-carbonyl] AR-A014418 by [11C]CO2 fixation

  摘要：

  The highly selective glycogen synthase kinase-3 (GSK-3) inhibitor N-(4-methoxybenzyl)-N'-(5-nitro-1,3-thiazol-2-yl) urea (AR-A014418) was radiolabeled with carbon-11 (C-11; half-life = 20.4 min) at the urea moiety via [C-11]CO2 fixation. Reaction of [C-11]CO2 with 4-methoxybenzylamine in the presence of a CO2 fixating base was followed by dehydration with POCl3 and addition of 2-amino-5-nitrothiazole to prepare [C-11-carbonyl] AR-A014418. This reaction resulted in an 8% uncorrected radiochemical yield, based on [C-11]CO2, with high specific activity (4 Ci/mu mol) within 30 min. An in vitro GSK-3 beta enzyme activity assay revealed that AR-A014418 (K-i = 770 nM) is not as potent as previously claimed. The [C-11]CO2 fixation methodology described herein should prove generally applicable to preparing 1-aryl-3-benzyl-[C-11-carbonyl] ureas as radiotracers for positron emission tomography. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.139