2-(1-(2,4,6-triisopropylphenylsulfonyl)aziridine-2-carboxamido)-N-methylcarbonyl-Val-βAla-Phe-Gly-NH2 | 1039309-54-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: 2-(1-(2,4,6-triisopropylphenylsulfonyl)aziridine-2-carboxamido)-N-methylcarbonyl-Val-βAla-Phe-Gly-NH2
• 英文别名: N-[2-[[(2S)-1-[[3-[[(2S)-1-[(2-amino-2-oxoethyl)amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-oxopropyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-2-oxoethyl]-1-[2,4,6-tri(propan-2-yl)phenyl]sulfonylaziridine-2-carboxamide
• CAS: 1039309-54-0
• 化学式: C₃₉H₅₇N₇O₈S
• 分子量: 783.99
• InChiKey: JPIMBHIBSFYCFN-PTUYRVDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  55
• 可旋转键数：
  20
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  234
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(1-(2,4,6-triisopropylphenylsulfonyl)aziridine-2-carboxamido)-N-methylcarbonyl-Val-βAla-Phe-Gly-NH2 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 0.25h， 生成 (RS)-3-[18F]fluoro-2-(2,4,6-triisopropylphenylsulfonamido)propanamide-N-methylcarbonyl-Val-βAla-Phe-Gly-NH2
  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：

  4-氟-3-三氟甲氧基苯甲酸 、 2-(1-(2,4,6-triisopropylphenylsulfonyl)aziridine-2-carboxamido)acetic acid 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， 以20 mg的产率得到2-(1-(2,4,6-triisopropylphenylsulfonyl)aziridine-2-carboxamido)-N-methylcarbonyl-Val-βAla-Phe-Gly-NH2
  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。