[¹⁸F]N-[2-[N-ethyl-N-[(E)-4-fluorobut-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide | 1472065-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: [¹⁸F]N-[2-[N-ethyl-N-[(E)-4-fluorobut-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• 英文别名: N-[2-[ethyl-[(E)-4-(18F)fluoranylbut-2-enyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• CAS: 1472065-85-2
• 化学式: C₁₇H₂₀FIN₄O
• 分子量: 441.276
• InChiKey: GHASTSFKWBGDKA-OBKRMRTNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-[(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-yl]-N-ethyl-1,2-ethylenediamine 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 [¹⁸F]N-[2-[N-ethyl-N-[(E)-4-fluorobut-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
  参考文献：
  名称：

  Synthesis, Radiofluorination, and in Vivo Evaluation of Novel Fluorinated and Iodinated Radiotracers for PET Imaging and Targeted Radionuclide Therapy of Melanoma

  摘要：

  Our project deals with a multimodal approach using a single fluorinated and iodinated melanin-targeting structure and offering both imaging (positron emission tomography (PET)/fluorine-18) and treatment (targeted radionuclide therapy/iodine-131) of melanoma. Six 6-iodoquinoxaline-2-carboxamide derivatives with various side chains bearing fluorine were synthesized and radiofluorinated, and their in vivo biodistribution was studied by PET imaging in B16B16 primary melanoma-bearing mice. Among this series, [F-18]8 emerged as the most promising compound. [18F]8 was obtained by a fully automated radiosynthesis process within 57 min with an overall radiochemical yield of 21%, decay-corrected. PET imaging of [18F]8 demonstrated very encouraging results as early as 1 h postinjection with high tumor uptake (14.33% +/- 2.11% ID/g), high contrast (11.04 +/- 2.87 tumor-to-muscle ratio), and favorable clearance properties. These results, associated with the previously reported pharmacokinetic properties and dosimetry of 8, make it a potential agent for both PET imaging and targeted radionuclide therapy of melanoma.

  DOI：

  10.1021/jm400877v

文献信息

• Synthesis, Radiofluorination, and <i>in Vivo</i> Evaluation of Novel Fluorinated and Iodinated Radiotracers for PET Imaging and Targeted Radionuclide Therapy of Melanoma
  作者：Emilie M. F. Billaud、Latifa Rbah-Vidal、Aurélien Vidal、Sophie Besse、Sébastien Tarrit、Serge Askienazy、Aurélie Maisonial、Nicole Moins、Jean-Claude Madelmont、Elisabeth Miot-Noirault、Jean-Michel Chezal、Philippe Auzeloux

  DOI：10.1021/jm400877v

  日期：2013.11.14

  Our project deals with a multimodal approach using a single fluorinated and iodinated melanin-targeting structure and offering both imaging (positron emission tomography (PET)/fluorine-18) and treatment (targeted radionuclide therapy/iodine-131) of melanoma. Six 6-iodoquinoxaline-2-carboxamide derivatives with various side chains bearing fluorine were synthesized and radiofluorinated, and their in vivo biodistribution was studied by PET imaging in B16B16 primary melanoma-bearing mice. Among this series, [F-18]8 emerged as the most promising compound. [18F]8 was obtained by a fully automated radiosynthesis process within 57 min with an overall radiochemical yield of 21%, decay-corrected. PET imaging of [18F]8 demonstrated very encouraging results as early as 1 h postinjection with high tumor uptake (14.33% +/- 2.11% ID/g), high contrast (11.04 +/- 2.87 tumor-to-muscle ratio), and favorable clearance properties. These results, associated with the previously reported pharmacokinetic properties and dosimetry of 8, make it a potential agent for both PET imaging and targeted radionuclide therapy of melanoma.