N-[2-[N-ethyl-N-[(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide | 1472065-94-3

• 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: N-[2-[N-ethyl-N-[(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• 英文别名: N-[2-[[(E)-4-[tert-butyl(dimethyl)silyl]oxybut-2-enyl]-ethylamino]ethyl]-6-iodoquinoxaline-2-carboxamide
• CAS: 1472065-94-3
• 化学式: C₂₃H₃₅IN₄O₂Si
• 分子量: 554.546
• InChiKey: ZNRKBNHXUJZRTG-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.86
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[2-[N-ethyl-N-[(E)-4-(tert-butyldimethylsilyloxy)but-2-en-1-yl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以99%的产率得到N-[2-[N-ethyl-N-[(E)-4-hydroxybut-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
• 作为产物：
  描述：

  4-(tert-butyldimethylsilyloxy)-2-butyn-1-ol 在 咪唑 、 cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate 、 三乙氧基硅烷 、 碘 、 potassium carbonate 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 113.17h， 生成 N-[2-[N-ethyl-N-[(E)-4-(tert-butyldimethylsilyloxy)but-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