[3-(hex-5-ynyloxy)pyridin-2-yl]trimethylammonium trifluoromethanesulfonate | 1174914-29-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [3-(hex-5-ynyloxy)pyridin-2-yl]trimethylammonium trifluoromethanesulfonate
• 英文别名: (3-Hex-5-ynoxypyridin-2-yl)-trimethylazanium;trifluoromethanesulfonate
• CAS: 1174914-29-4
• 化学式: CF₃O₃S*C₁₄H₂₁N₂O
• 分子量: 382.404
• InChiKey: OTKQUXPIFGHVBV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  87.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [3-(hex-5-ynyloxy)pyridin-2-yl]trimethylammonium trifluoromethanesulfonate 在 Kryptofix222[18F]钾盐 作用下， 以 二甲基亚砜 为溶剂， 反应 0.25h， 生成 2-[18F]fluoro-3-(hex-5-ynyloxy)pyridine
  参考文献：
  名称：

  Radiosynthesis and bioconjugation of [¹⁸F]FPy5yne, a prosthetic group for the¹⁸F labeling of bioactive peptides

  摘要：

  一种基于18F的新型支架已被制备用于标记叠氮化修饰的多肽，以便在PET成像中使用。2-[18F]氟-3-(己-5-炔氧基)吡啶([18F]FPy5yne，[18F]-1)是通过有效的亲核杂环芳香族取代反应制备的，使用相应的2-硝基(2)或2-三甲基铵三氟甲磺酸盐吡啶(3)。从2中获得的[18F]FPy5yne的最佳放射化学产率为91%(射线TLC，15分钟，110°C，DMSO)。从3中获得的最佳放射化学产率为93%(射线TLC，15分钟，110°C，MeCN)。通过HPLC纯化的[18F]FPy5yne通过CuI介导的Huisgen [3+2]环加成反应与模型多肽N3–(CH2)4–CO–YKRI–OH连接，在铜稳定配体三(苄基三唑基甲基)胺(TBTA)和N,N-二异丙基乙胺(DIEA)的存在下。生物共轭物的放射化学产率平均为89%±8.6%(n=4)，通过放射HPLC判断。从轰击结束时获得的未衰减校正的最佳收集放射化学产率为5.8%(衰减校正后为18.7%)，总制备时间为160分钟。版权所有 © 2008 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1561
• 作为产物：
  描述：

  2-dimethylamino-3-(hex-5-ynyloxy)pyridine 、 三氟甲烷磺酸甲酯 以 甲苯 为溶剂， 以95%的产率得到[3-(hex-5-ynyloxy)pyridin-2-yl]trimethylammonium trifluoromethanesulfonate
  参考文献：
  名称：

  Radiosynthesis and bioconjugation of [¹⁸F]FPy5yne, a prosthetic group for the¹⁸F labeling of bioactive peptides

  摘要：

  一种基于18F的新型支架已被制备用于标记叠氮化修饰的多肽，以便在PET成像中使用。2-[18F]氟-3-(己-5-炔氧基)吡啶([18F]FPy5yne，[18F]-1)是通过有效的亲核杂环芳香族取代反应制备的，使用相应的2-硝基(2)或2-三甲基铵三氟甲磺酸盐吡啶(3)。从2中获得的[18F]FPy5yne的最佳放射化学产率为91%(射线TLC，15分钟，110°C，DMSO)。从3中获得的最佳放射化学产率为93%(射线TLC，15分钟，110°C，MeCN)。通过HPLC纯化的[18F]FPy5yne通过CuI介导的Huisgen [3+2]环加成反应与模型多肽N3–(CH2)4–CO–YKRI–OH连接，在铜稳定配体三(苄基三唑基甲基)胺(TBTA)和N,N-二异丙基乙胺(DIEA)的存在下。生物共轭物的放射化学产率平均为89%±8.6%(n=4)，通过放射HPLC判断。从轰击结束时获得的未衰减校正的最佳收集放射化学产率为5.8%(衰减校正后为18.7%)，总制备时间为160分钟。版权所有 © 2008 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1561

文献信息

• Labeling of an Antisense Oligonucleotide with [¹⁸F]FPy5yne
  作者：James A. H. Inkster、Michael J. Adam、Tim Storr、Thomas J. Ruth

  DOI：10.1080/15257770903400691

  日期：2009.12.7

  Functional imaging of gene expression in vivo with short-lived positron emitter F-18 remains an unrealized goal, in part because the long reaction times and challenging protocols typically required to label nucleic acid-based molecular probes with this radionuclide (t(1/2) = 109.8 minutes). To this end, we synthesized prosthetic group 2-[F-18] fluoro-3-(hex-5-ynyloxy) pyridine ([F-18] FPy5yne), used previously to label peptides, and coupled it to an oligodeoxyribonucleotide with F-18 by way of a Cu-I-mediated azide/alkyne cycloaddition reaction. HPLC-purified [F-18]FPy5yne was ligated to a 5'-azide-modified DNA sequence antisense to mdr1 mRNA in the presence of Cu-I-stabilizing ligand tris(benzyltriazolylmethyl) amine and 2,6-lutidine. Non-decay corrected, collected yields of the F-18-labeled oligonucleotide from end-of-bombardment were 3.9% +/- 0.5% (n = 3; 24.6% 0.5% decay corrected). Shortest preparation time was 276 minutes from start of synthesis.
• 2-Fluoropyridine prosthetic compounds for the 18F labeling of bombesin analogues
  作者：James Inkster、Kuo-Shyan Lin、Samia Ait-Mohand、Simon Gosselin、François Bénard、Brigitte Guérin、Maral Pourghiasian、Thomas Ruth、Paul Schaffer、Tim Storr

  DOI：10.1016/j.bmcl.2013.04.060

  日期：2013.7

  Acetylene-bearing 2-[F-18]fluoropyridines [F-18]FPy5yne and PEG-[F-18]FPyKYNE were prepared via efficient nucleophilic heteroaromatic [F-18]fluorination of their corresponding 2-trimethylammoniumpyrdinyl precursors. The prosthetic groups were conjugated to azide- and PEG(3)-modified bombesin(6-14) analogues via copper-catalyzed azide-alkyne cycloaddition couplings to yield mono- and di-mini-PEGylated ligands for PET imaging of the gastrin- releasing peptide receptor. The PEG(3)- and PEG(2)/PEG(3)-bearing F-18 peptides showed decreased lipophilicity relative to an analogous non-mini-PEGylated F-18 peptide. Assessment of water-soluble peptide pharmacokinetics and tumour-targeting capabilities in a mouse model of prostate cancer is currently underway. (c) 2013 Elsevier Ltd. All rights reserved.
• Radiosynthesis and bioconjugation of [¹⁸F]FPy5yne, a prosthetic group for the¹⁸F labeling of bioactive peptides
  作者：James A. H. Inkster、Brigitte Guérin、Thomas J. Ruth、Michael J. Adam

  DOI：10.1002/jlcr.1561

  日期：2008.11

  A new 18F-based prosthetic group has been prepared for the labeling of azide-modified peptides for use in PET imaging. 2-[18F]fluoro-3-(hex-5-ynyloxy)pyridine ([18F]FPy5yne, [18F]-1) was prepared via efficient nucleophilic heteroaromatic substitution of either the corresponding 2-nitro (2) or 2-trimethylammonium trifluoromethanesulfonate pyridine (3). Best radiochemical yield of [18F]FPy5yne from 2 was 91% by radioTLC (15 min, 110°C, DMSO). From 3, best radiochemical yield by radioTLC was 93% (15 min, 110°C, MeCN). HPLC-purified [18F]FPy5yne was ligated to model peptide N3–(CH2)4–CO–YKRI–OH by way of CuI-mediated Huisgen [3+2] cycloaddition in the presence of copper-stabilizing ligand tris(benzyltriazolylmethyl)amine (TBTA) and N,N-diisopropylethylamine (DIEA). Bioconjugate radiochemical yields were obtained in average yields of 89%±8.6% (n=4), as judged by radioHPLC. Best non-decay-corrected, collected radiochemical yield of modified peptide from end-of-bombardment was 5.8% (18.7% decay-corrected), with a total preparation time of 160 min from start of synthesis. Copyright © 2008 John Wiley & Sons, Ltd.

  一种基于18F的新型支架已被制备用于标记叠氮化修饰的多肽，以便在PET成像中使用。2-[18F]氟-3-(己-5-炔氧基)吡啶([18F]FPy5yne，[18F]-1)是通过有效的亲核杂环芳香族取代反应制备的，使用相应的2-硝基(2)或2-三甲基铵三氟甲磺酸盐吡啶(3)。从2中获得的[18F]FPy5yne的最佳放射化学产率为91%(射线TLC，15分钟，110°C，DMSO)。从3中获得的最佳放射化学产率为93%(射线TLC，15分钟，110°C，MeCN)。通过HPLC纯化的[18F]FPy5yne通过CuI介导的Huisgen [3+2]环加成反应与模型多肽N3–(CH2)4–CO–YKRI–OH连接，在铜稳定配体三(苄基三唑基甲基)胺(TBTA)和N,N-二异丙基乙胺(DIEA)的存在下。生物共轭物的放射化学产率平均为89%±8.6%(n=4)，通过放射HPLC判断。从轰击结束时获得的未衰减校正的最佳收集放射化学产率为5.8%(衰减校正后为18.7%)，总制备时间为160分钟。版权所有 © 2008 John Wiley & Sons, Ltd.