N-[2-[[N-ethyl-N-3-(2-fluoropyridin-4-yl)propyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide | 1176209-64-5

• 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-3-(2-fluoropyridin-4-yl)propyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• 英文别名: N-[2-[ethyl-[3-(2-fluoropyridin-4-yl)propyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide
• CAS: 1176209-64-5
• 化学式: C₂₁H₂₃FIN₅O
• 分子量: 507.349
• InChiKey: GXHLCNNPAFDLTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-[[N-ethyl-N-3-(2-fluoropyridin-4-yl)propyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 12.17h， 以84%的产率得到N-[2-[[N-ethyl-N-3-(2-fluoropyridin-4-yl)propyl]amino]ethyl]-6-iodoquinoxaline-2-carboxamide dihydrochloride
  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
• 作为产物：
  描述：

  2-fluoro-4-(3-hydroxypropyl)pyridine 在 三甲基铝 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 正庚烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 45.08h， 生成 N-[2-[[N-ethyl-N-3-(2-fluoropyridin-4-yl)propyl]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。
• US9125937B2
  申请人：——

  公开号：US9125937B2

  公开（公告）日：2015-09-08
• [EN] LABELLED ANALOGUES OF HALOBENZAMIDES AS MULTIMODAL RADIOPHARMACEUTICALS AND THEIR PRECURSORS<br/>[FR] ANALOGUES MARQUÉS D'HALOGÉNO-BENZAMIDES EN TANT QUE PRODUITS RADIOPHARMACEUTIQUES MULTIMODAUX ET LEURS PRÉCURSEURS
  申请人：INST NAT SANTE RECH MED

  公开号：WO2009095872A2

  公开（公告）日：2009-08-06

  The present invention relates to the compound of formula (I): in which R1 represents a hydrogen atom, an optionally labelled halogen, a radionuclide or a Sn[(C1 -C4 )alkyl]3 group, Ar represents an aryl group or a heteroaryl group, R9 represents a hydrogen atom, a (C1 -C4 )alkyl group or forms together with the group R1 -Ar a ring fused with the Ar group, A represents a group of formula (β) or (δ): R3 and R4 independently represent a hydrogen atom, a (C1 -C6 )alkyl group, a (C1 -C6 )alkenyl group or a group of formula (y): wherein R11 represents an optionally labelled halogen, a radionuclide, an aryl or heteroaryl group optionally substituted by an optionally labelled halogen, a radionuclide, a -NO2 group, a -NR5 R6 group, a N+R5R6R7X- group, or a -OSO2R12 group, and their addition salts with pharmaceutically acceptable acids. The present invention also relates to pharmaceutical compositions comprising themand to their use in diagnosis, in particular with SPECTor PET imaging and in therapyofmelanoma, viatargeted radionuclide therapy.
• 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.