N-[2-(2-(18F)fluoranylethoxy)-4,6-dimethoxypyrimidin-5-yl]-5-[(3,3,6-trimethyl-1,2-dihydroinden-5-yl)oxy]furan-2-carboxamide | 1595292-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[2-(2-(18F)fluoranylethoxy)-4,6-dimethoxypyrimidin-5-yl]-5-[(3,3,6-trimethyl-1,2-dihydroinden-5-yl)oxy]furan-2-carboxamide
• CAS: 1595292-21-9
• 化学式: C₂₅H₂₈FN₃O₆
• 分子量: 484.514
• InChiKey: PVGVKMIGQPWHEG-KPVNRNJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-氯-4,6-二甲氧基-5-硝基嘧啶 在 kryptofix 222 、 铁粉 、 sodium hydride 、 氯化铵 、 三乙胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 生成 N-[2-(2-(18F)fluoranylethoxy)-4,6-dimethoxypyrimidin-5-yl]-5-[(3,3,6-trimethyl-1,2-dihydroinden-5-yl)oxy]furan-2-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of small-molecule [18F] labeled gonadotropin-releasing hormone (GnRH) receptor antagonists as potential PET imaging agents for GnRH receptor expression

  摘要：

  Two novel small molecule gonadotropin-releasing hormone (GnRH) receptor antagonists (12 and 13) of the furamide-class were synthesized and evaluated in vitro for their receptor binding affinities for the rat GnRH receptor. Radiolabeling with no carrier added fluorine-18 of the appropriate precursors was investigated in a one-step reaction. LogP (Octanol/PBS pH 7.4) and serum stability of the compounds were investigated. The antagonists showed low nM affinity for the rat GnRH receptor. F-18-radiolabled compounds were obtained in high radiochemical purity (> 95%) and specific activity (> 75 GBq/mu mol). These findings suggest this class of compounds holds promise as potential probes for PET targeting of GnRHreceptor expression. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.002

文献信息

• RADIOLABELED GNRH ANTAGONISTS AS PET IMAGING AGENTS
  申请人：OSLO UNIVERSITETSSYKEHUS HF

  公开号：US20160058895A1

  公开（公告）日：2016-03-03

  Provided herein is technology relating to imaging agents for positron emission tomography (PET) and particularly, but not exclusively, to a gonadotropin-releasing hormone (GnRH) antagonist radiolabeled with positron emitting nuclides and to methods of visualizing GnRH receptors in the central nervous system by PET from administration of such compounds to warm-blooded animals for diagnostic purposes.
• Synthesis and in vitro evaluation of small-molecule [18F] labeled gonadotropin-releasing hormone (GnRH) receptor antagonists as potential PET imaging agents for GnRH receptor expression
  作者：Dag Erlend Olberg、Kjetil Wessel Andressen、Finn Olav Levy、Jo Klaveness、Ira Haraldsen、Julie L. Sutcliffe

  DOI：10.1016/j.bmcl.2014.02.002

  日期：2014.4

  Two novel small molecule gonadotropin-releasing hormone (GnRH) receptor antagonists (12 and 13) of the furamide-class were synthesized and evaluated in vitro for their receptor binding affinities for the rat GnRH receptor. Radiolabeling with no carrier added fluorine-18 of the appropriate precursors was investigated in a one-step reaction. LogP (Octanol/PBS pH 7.4) and serum stability of the compounds were investigated. The antagonists showed low nM affinity for the rat GnRH receptor. F-18-radiolabled compounds were obtained in high radiochemical purity (> 95%) and specific activity (> 75 GBq/mu mol). These findings suggest this class of compounds holds promise as potential probes for PET targeting of GnRHreceptor expression. (c) 2014 Elsevier Ltd. All rights reserved.