3-(18F)fluoranyl-N-[2-[3-[3-[(2R,4S,5R)-4-(1-methoxycyclohexyl)oxy-5-[(1-methoxycyclohexyl)oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propylamino]-2-oxoethyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanamide

• 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: 3-(18F)fluoranyl-N-[2-[3-[3-[(2R,4S,5R)-4-(1-methoxycyclohexyl)oxy-5-[(1-methoxycyclohexyl)oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propylamino]-2-oxoethyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanamide
• 化学式: C₅₂H₇₉N₁₄O₁₀Pol
• 分子量: 935.2
• InChiKey: LJVJMOCARXGLLS-UTMZUCTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  65
• 可旋转键数：
  22
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  200
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  [2-(R,S)-3-fluoro-2-(2,4,6-triisopropyl-benzenesulfonylamino)-propanamido]-acetic acid 、 3-(18F)fluoranyl-N-[2-[3-[3-[(2R,4S,5R)-4-(1-methoxycyclohexyl)oxy-5-[(1-methoxycyclohexyl)oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propylamino]-2-oxoethyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanamide 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成
  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
• 作为产物：
  描述：

  N-[2-[3-[3-[(2R,4S,5R)-4-(1-methoxycyclohexyl)oxy-5-[(1-methoxycyclohexyl)oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propylamino]-2-oxoethyl]-1-[2,4,6-tri(propan-2-yl)phenyl]sulfonylaziridine-2-carboxamide 在 potassium [¹⁸F]fluoride 、 caesium carbonate 、 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 0.33h， 生成 3-(18F)fluoranyl-N-[2-[3-[3-[(2R,4S,5R)-4-(1-methoxycyclohexyl)oxy-5-[(1-methoxycyclohexyl)oxymethyl]oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]propylamino]-2-oxoethyl]-2-[[2,4,6-tri(propan-2-yl)phenyl]sulfonylamino]propanamide
  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