[125I]N-[2-[[N-ethyl-N-(6-fluoropyridin-2-yl)]amino]ethyl]-6-iodoquinoxaline-2-carboxamide | 1176210-24-4

• 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: [125I]N-[2-[[N-ethyl-N-(6-fluoropyridin-2-yl)]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• 英文别名: N-[2-[ethyl-(6-fluoropyridin-2-yl)amino]ethyl]-6-(125I)iodanylquinoxaline-2-carboxamide
• CAS: 1176210-24-4
• 化学式: C₁₈H₁₇FIN₅O
• 分子量: 463.364
• InChiKey: TVNWVHYAJPPGQM-STTHPYEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-[2-[[N-ethyl-N-(6-fluoropyridin-2-yl)]amino]ethyl]-6-iodoquinoxaline-2-carboxamide 在 sodium iodide 、 copper(II) sulfate 作用下， 反应 1.0h， 生成 [125I]N-[2-[[N-ethyl-N-(6-fluoropyridin-2-yl)]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
  参考文献：
  名称：

  Single Photon Emission Computed Tomography/Positron Emission Tomography Imaging and Targeted Radionuclide Therapy of Melanoma: New Multimodal Fluorinated and Iodinated Radiotracers

  摘要：

  This study reports a series of 14 new iodinated and fluorinated compounds offering both early imaging (I-123, I-124, F-18) and systemic treatment (I-131) of melanoma potentialities. The biodistribution of each I-125-labeled tracer was evaluated in a model of melanoma B16F0 bearing mice, using in vivo serial gamma scintigraphic imaging. Among this series, [I-125]56 emerged as the most promising compound in terms of specific tumoral uptake and in vivo kinetic profile. To validate our multimodality concept, the radiosynthesis of [F-18]56 was then optimized and this radiotracer has been successfully investigated for in vivo PET imaging of melanoma in B16F0- and B16F10-bearing mouse model. The therapeutic efficacy of [I-131]56 was then evaluated in mice bearing subcutaneous B16F0 melanoma, and a significant slow down in tumoral growth was demonstrated. These data support further development of 56 for PET imaging (F-18, I-124) and targeted radionuclide therapy (I-131) of melanoma using a single chemical structure.

  DOI：

  10.1021/jm101574q

文献信息

• LABELLED ANALOGUES OF HALOBENZAMIDES AS MULTIMODAL RADIOPHARMACEUTICALS AND THEIR PRECURSORS
  申请人：Chezal Jean-Michel

  公开号：US20110044899A1

  公开（公告）日：2011-02-24

  A compound of formula (I): in which R 1 represents a hydrogen atom, an optionally labelled halogen, a radionuclide or a Sn[(C 1 -C 4 )alkyl] 3 group, Ar represents an aryl group or a heteroaryl group, R 9 represents a hydrogen atom, a (C 1 -C 4 ) alkyl group or forms together with the group R 1 —Ar a ring fused with the Ar group, A represents a group of formula (β) or (δ): R 3 and R 4 independently represent a hydrogen atom, a (C 1 -C 6 )alkyl group, a (C 1 -C 6 ) alkenyl group or a group of formula (y): wherein R 11 represents an optionally labelled halogen, a radionuclide, an aryl or heteroaryl group optionally substituted by an optionally labelled halogen, a radionuclide, a —NO 2 group, a —NR 5 R 6 group, a N + R 5 R 6 R 7 X − group, or a —OSO 2 R 12 group, and their addition salts with pharmaceutically acceptable acids.

  化合物的化学式为(I)：其中R1代表氢原子、可选择标记的卤素、放射性核素或Sn[(C1-C4)烷基]3基团，Ar代表芳基或杂芳基，R9代表氢原子、(C1-C4)烷基或与基团R1-Ar共同形成与Ar基团融合的环，A代表化学式(β)或(δ)的基团：R3和R4分别独立地代表氢原子、(C1-C6)烷基、(C1-C6)烯基或化学式(y)的基团：其中R11代表可选择标记的卤素、放射性核素、可选择取代的芳基或杂芳基，取代基可以是可选择标记的卤素、放射性核素、—NO2基团、—NR5R6基团、N+R5R6R7X−基团或—OSO2R12基团，以及它们与药物可接受的酸形成的加合物。
• Single Photon Emission Computed Tomography/Positron Emission Tomography Imaging and Targeted Radionuclide Therapy of Melanoma: New Multimodal Fluorinated and Iodinated Radiotracers
  作者：Aurélie Maisonial、Bertrand Kuhnast、Janine Papon、Raphaël Boisgard、Martine Bayle、Aurélien Vidal、Philippe Auzeloux、Latifa Rbah、Mathilde Bonnet-Duquennoy、Elisabeth Miot-Noirault、Marie-Josèphe Galmier、Michèle Borel、Serge Askienazy、Frédéric Dollé、Bertrand Tavitian、Jean-Claude Madelmont、Nicole Moins、Jean-Michel Chezal

  DOI：10.1021/jm101574q

  日期：2011.4.28

  This study reports a series of 14 new iodinated and fluorinated compounds offering both early imaging (I-123, I-124, F-18) and systemic treatment (I-131) of melanoma potentialities. The biodistribution of each I-125-labeled tracer was evaluated in a model of melanoma B16F0 bearing mice, using in vivo serial gamma scintigraphic imaging. Among this series, [I-125]56 emerged as the most promising compound in terms of specific tumoral uptake and in vivo kinetic profile. To validate our multimodality concept, the radiosynthesis of [F-18]56 was then optimized and this radiotracer has been successfully investigated for in vivo PET imaging of melanoma in B16F0- and B16F10-bearing mouse model. The therapeutic efficacy of [I-131]56 was then evaluated in mice bearing subcutaneous B16F0 melanoma, and a significant slow down in tumoral growth was demonstrated. These data support further development of 56 for PET imaging (F-18, I-124) and targeted radionuclide therapy (I-131) of melanoma using a single chemical structure.