[18F](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide | 1446701-47-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [18F](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
• 英文别名: [¹⁸F]BMS-754807；1-(4-((5-Cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo(2,1-F)(1,2,4)triazin-2-yl)-N-(6-(18F)fluoro-3-pyridinyl)-2-methyl-L-prolinamide；(2S)-1-[4-[(5-cyclopropyl-1H-pyrazol-3-yl)amino]pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N-(6-(18F)fluoranylpyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
• CAS: 1446701-47-8
• 化学式: C₂₃H₂₄FN₉O
• 分子量: 460.503
• InChiKey: LQVXSNNAFNGRAH-SXBFPYQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2-chloro-N-(5-cyclopropyl-1H-pyrazol-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4-amine 在 氯化亚砜 、 potassium tert-butylate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 [18F](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of [18F]BMS-754807: A potential PET ligand for IGF-1R

  摘要：

  Radiosynthesis and in vitro evaluation of [F-18](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[ 2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide ([F-18]BMS-754807 or [F-18]1) a specific IGF-1R inhibitor was performed. [F-18]1 demonstrated specific binding in vitro to human cancer tissues. Synthesis of reference standard 1 and corresponding bromo derivative (1a), the precursor for radiolabeling were achieved from 2,4-dichloropyrrolo[2,1-f][1,2,4] triazine (4) in three steps with 50% overall yield. The radioproduct was obtained in 8% yield by reacting 1a with [F-18]TBAF in DMSO at 170 degrees C at high radiochemical purity and specific activity (1-2 Ci/mu mol, N = 10). The proof of concept of IGF-IR imaging with [F-18]1 was demonstrated by in vitro autoradiography studies using pathologically identified surgically removed grade IV glioblastoma, breast cancer and pancreatic tumor tissues. These studies indicate that [F-18]1 can be a potential PET tracer for monitoring IGF-1R. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.026

文献信息

• Synthesis and in vitro evaluation of [18F]BMS-754807: A potential PET ligand for IGF-1R
  作者：Vattoly J. Majo、Victoria Arango、Norman R. Simpson、Jaya Prabhakaran、Suham A. Kassir、Mark D. Underwood、Mihran Bakalian、Peter Canoll、J. John Mann、J.S. Dileep Kumar

  DOI：10.1016/j.bmcl.2013.05.026

  日期：2013.7

  Radiosynthesis and in vitro evaluation of [F-18](S)-1-(4-((5-cyclopropyl-1H-pyrazol-3-yl)amino)pyrrolo[ 2,1-f][1,2,4]triazin-2-yl)-N-(6-fluoropyridin-3-yl)-2-methylpyrrolidine-2-carboxamide ([F-18]BMS-754807 or [F-18]1) a specific IGF-1R inhibitor was performed. [F-18]1 demonstrated specific binding in vitro to human cancer tissues. Synthesis of reference standard 1 and corresponding bromo derivative (1a), the precursor for radiolabeling were achieved from 2,4-dichloropyrrolo[2,1-f][1,2,4] triazine (4) in three steps with 50% overall yield. The radioproduct was obtained in 8% yield by reacting 1a with [F-18]TBAF in DMSO at 170 degrees C at high radiochemical purity and specific activity (1-2 Ci/mu mol, N = 10). The proof of concept of IGF-IR imaging with [F-18]1 was demonstrated by in vitro autoradiography studies using pathologically identified surgically removed grade IV glioblastoma, breast cancer and pancreatic tumor tissues. These studies indicate that [F-18]1 can be a potential PET tracer for monitoring IGF-1R. (C) 2013 Elsevier Ltd. All rights reserved.