3-fluoro-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 | 1039309-78-8

• 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-fluoro-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
• CAS: 1039309-78-8
• 化学式: C₄₇H₇₄FN₅O₁₁S
• 分子量: 936.196
• InChiKey: LJVJMOCARXGLLS-MQSCWBNBSA-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 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 0.5h， 以16%的产率得到3-fluoro-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

文献信息

• Radiolabelling via fluorination of aziridines
  申请人：Srinivasan Ananth

  公开号：US20090022664A1

  公开（公告）日：2009-01-22

  The present invention relates to novel compounds suitable for or already radiolabelled with 18 F, methods of making such compounds and use of such compounds for diagnostic imaging.

  本发明涉及适用于或已经标记为18F的新化合物，制备这种化合物的方法以及将这种化合物用于诊断成像的用途。
• 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.