[(3-(2-(prop-2-ynyloxy)ethoxy)ethoxy)pyridine-2yl]trimethylammonium trifluoromethanesulfonate | 1443654-81-6

• 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-(2-(prop-2-ynyloxy)ethoxy)ethoxy)pyridine-2yl]trimethylammonium trifluoromethanesulfonate
• 英文别名: Trifluoromethanesulfonate;trimethyl-[3-[2-(2-prop-2-ynoxyethoxy)ethoxy]pyridin-2-yl]azanium；trifluoromethanesulfonate;trimethyl-[3-[2-(2-prop-2-ynoxyethoxy)ethoxy]pyridin-2-yl]azanium
• CAS: 1443654-81-6
• 化学式: CF₃O₃S*C₁₅H₂₃N₂O₃
• 分子量: 428.43
• InChiKey: REEMTFVWIBDVAU-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(3-(2-(prop-2-ynyloxy)ethoxy)ethoxy)pyridine-2yl]trimethylammonium trifluoromethanesulfonate 在 [¹⁸F]fluoride 、 potassium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.72h， 生成 2-(fluoro-18F)-3-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)pyridine
  参考文献：
  名称：

  2-Fluoropyridine prosthetic compounds for the 18F labeling of bombesin analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.04.060
• 作为产物：
  描述：

  2-[2-(2-丙炔氧基)乙氧基]乙醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 54.0h， 生成 [(3-(2-(prop-2-ynyloxy)ethoxy)ethoxy)pyridine-2yl]trimethylammonium trifluoromethanesulfonate
  参考文献：
  名称：

  2-Fluoropyridine prosthetic compounds for the 18F labeling of bombesin analogues

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2013.04.060

文献信息

• 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.