¹⁸F-5-fluoro-N-(2-[diethylamino]ethyl)picolinamide | 1373930-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: ¹⁸F-5-fluoro-N-(2-[diethylamino]ethyl)picolinamide
• 英文别名: N-(2-(diethylamino)-ethyl)-5-[18F]fluoropicolinamide；N-[2-(diethylamino)ethyl]-5-(18F)fluoranylpyridine-2-carboxamide
• CAS: 1373930-34-7
• 化学式: C₁₂H₁₈FN₃O
• 分子量: 238.294
• InChiKey: TWRNBUQZDSVURX-HSGWXFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴-N-(2-(二乙基氨基)乙基)-2-吡啶甲酰胺 在 [18F]-fluoride 、 potassium 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 、 乙腈 为溶剂， 反应 0.17h， 生成 ¹⁸F-5-fluoro-N-(2-[diethylamino]ethyl)picolinamide
  参考文献：
  名称：

  Development of ¹⁸F-Labeled Picolinamide Probes for PET Imaging of Malignant Melanoma

  摘要：

  Melanoma is an aggressive skin cancer with worldwide increasing incidence. Development of positron emission tomography (PET) probes for early detection of melanoma is critical for improving the survival rate of melanoma patients. In this research, F-18-picolinamide-based PET probes were prepared by direct radiofluorination of the bromopicolinamide precursors using no-carrier-added F-18-fluoride. The resulting probes, F-18-1, F-18-2 and F-18-3, were then evaluated in vivo by small animal PET imaging and biodistribution studies in C57BL/6 mice bearing B16F10 murine melanoma tumors. Noninvasive small animal PET studies demonstrated excellent tumor imaging contrasts for all probes, while F-18-2 showed higher tumor to muscle ratios than F-18-1 and F-18-3. Furthermore, F-18-2 demonstrated good in vivo stability as evidenced by the low bone uptake in biodistribution studies. Collectively, these findings suggest F-18-2 as a highly promising PET probe for translation into clinical detection of melanoma.

  DOI：

  10.1021/jm301740k

文献信息

• Ring-Closing Synthesis of Dibenzothiophene Sulfonium Salts and Their Use as Leaving Groups for Aromatic ¹⁸F-Fluorination
  作者：Thibault Gendron、Kerstin Sander、Klaudia Cybulska、Laure Benhamou、Pak Kwan Brian Sin、Aqsa Khan、Michael Wood、Michael J. Porter、Erik Årstad

  DOI：10.1021/jacs.8b06730

  日期：2018.9.5

  Herein, we report a novel intramolecular ring-closing reaction of biaryl thioethers that give access to highly functionalized dibenzothiophene sulfonium salts under mild conditions. The resulting precursors react regioselectively with [18F]fluoride to give [18F]fluoroarenes in predictable radiochemical yields. The strategy expands the available radiochemical space and provides superior labeling efficiency

  在此，我们报道了联芳基硫醚的一种新型分子内闭环反应，该反应可以在温和条件下获得高度官能化的二苯并噻吩锍盐。所得前体与[ 18 F]氟化物发生区域选择性反应，以可预测的放射化学产率生成[ 18 F]氟芳烃。该策略扩大了可用的放射化学空间，并为临床相关 PET 示踪剂提供了卓越的标记效率。
• Development, Optimization, and Scope of the Radiosynthesis of 3/5-[¹⁸F]Fluoropyridines from Readily Prepared Aryl(pyridinyl) Iodonium Salts: The Importance of TEMPO and K₂CO₃
  作者：Mathilde Pauton、Catherine Aubert、Guillaume Bluet、Florence Gruss-Leleu、Sébastien Roy、Cécile Perrio

  DOI：10.1021/acs.oprd.9b00021

  日期：2019.5.17

  A robust process for the radiosynthesis of 3/5-[F-18]fluoropyridines has been developed by radiofluorination of iodonium triflates using (KF)-F-18/(KCO3)-C-2/K-222 complex in the presence of TEMPO. Both electronically deficient and enriched iodonium salts were readily obtained from the corresponding 3/5-iodopyridines and afforded the corresponding 3/5-[F-18]fluoropyridines in 6-78% yields. The concentrations of K2CO3 and TEMPO were found to be crucial for the radiofluorination efficiency. The process was validated using two automated systems for the F-18-radiolabeling of 2-chloro and 2-carboxamido-5-fluoropyridines carried out in 10-20% yields.