N-benzyl-2-(3,4-dimethoxyphenylsulfonylamino)-3-fluoropropanamide | 1039309-62-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyl-2-(3,4-dimethoxyphenylsulfonylamino)-3-fluoropropanamide
• 英文别名: N-Benzyl-2-(3,4-dimethoxy-benzenesulfonylamino)-3-fluoro-propionamide；N-benzyl-2-[(3,4-dimethoxyphenyl)sulfonylamino]-3-fluoropropanamide
• CAS: 1039309-62-0
• 化学式: C₁₈H₂₁FN₂O₅S
• 分子量: 396.44
• InChiKey: CXZSLCHYTSHVFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-benzyl-1-(3,4-dimethoxyphenylsulfonyl)aziridine-2-carboxamide 在 potassium fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以23%的产率得到N-benzyl-2-(3,4-dimethoxyphenylsulfonylamino)-3-fluoropropanamide
  参考文献：
  名称：

  Nucleophilic ring-opening of activated aziridines: A one-step method for labeling biomolecules with fluorine-18

  摘要：

  The direct labeling of biomolecules with fluorine-18 is highly desirable. An option is the ring-opening of an activated aziridine moiety in a biomolecule using (18)F-fluoride. Therefore, a series of aziridine-based model compounds and three aziridine-based biomolecules four aziridine-based model compounds were synthesized and evaluated as potential precursors for a direct one-step radiolabeling with fluorine-18. High to moderate yields of (18)F-incorporation were achieved under mild labeling conditions. The influence of different activating groups, reaction temperature, solvent and base was investigated. The applicability of this method for the direct (18)F-radiolabeling of biomolecules for positron emission tomography (PET) studies is illustrated with examples. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.07.003

文献信息

• Radiolabelling via fluorination of aziridines
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1944288A1

  公开（公告）日：2008-07-16

  This invention relates to novel compounds comprising arziridine ring suitable for labelling or already labelled with an appropriate halogen, preferably 18F, methods of preparing such compounds, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging, preferably positron emission tomography (PET).

  这项发明涉及含有阿齐啶环的新化合物，适用于标记或已经用适当的卤素标记，优选为18F，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及这种化合物、组合物或试剂盒用于诊断成像，优选为正电子发射断层扫描（PET）的用途。
• [EN] RADIOLABELLING VIA FLUORINATION OF AZIRIDINES<br/>[FR] RADIOMARQUAGE PAR FLUORATION D'AZIRIDINES
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2008083729A1

  公开（公告）日：2008-07-17

  [EN] The present invention relates to novel compounds suitable for or already radiolabeled with ¹⁸F, methods of making such compounds and use of such compounds for diagnostic imaging.
  [FR] L'invention concerne de nouveaux composés déjà radiomarqués ou destinés au radiomarquage par ¹⁸F, des procédés de préparation de ces composés et leur utilisation dans l'imagerie diagnostique.
• Nucleophilic ring-opening of activated aziridines: A one-step method for labeling biomolecules with fluorine-18
  作者：Ulrike Roehn、Jessica Becaud、Linjing Mu、Ananth Srinivasan、Timo Stellfeld、Ansgar Fitzner、Keith Graham、Ludger Dinkelborg、August P. Schubiger、Simon M. Ametamey

  DOI：10.1016/j.jfluchem.2009.07.003

  日期：2009.10

  The direct labeling of biomolecules with fluorine-18 is highly desirable. An option is the ring-opening of an activated aziridine moiety in a biomolecule using (18)F-fluoride. Therefore, a series of aziridine-based model compounds and three aziridine-based biomolecules four aziridine-based model compounds were synthesized and evaluated as potential precursors for a direct one-step radiolabeling with fluorine-18. High to moderate yields of (18)F-incorporation were achieved under mild labeling conditions. The influence of different activating groups, reaction temperature, solvent and base was investigated. The applicability of this method for the direct (18)F-radiolabeling of biomolecules for positron emission tomography (PET) studies is illustrated with examples. (C) 2009 Elsevier B.V. All rights reserved.