N-(2-(18F)fluoro-3-phenylpropyl)-N-methylprop-2-yn-1-amine | 1146973-00-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(2-(18F)fluoro-3-phenylpropyl)-N-methylprop-2-yn-1-amine
• 英文别名: 2-(18F)fluoranyl-N-methyl-3-phenyl-N-prop-2-ynylpropan-1-amine
• CAS: 1146973-00-3
• 化学式: C₁₃H₁₆FN
• 分子量: 204.277
• InChiKey: HIULHOMMWRVCKA-UMSOTBISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-2-(N,N-methylpropargylamino)-3-phenylpropan-1-ol 在 甲基磺酰氯 、 三乙胺 、 potassium [¹⁸F]fluoride 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 0.33h， 生成 N-[(2S)-1-[18F]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine 、 N-(2-(18F)fluoro-3-phenylpropyl)-N-methylprop-2-yn-1-amine
  参考文献：
  名称：

  Synthesis of Three Novel Fluorine-18 Labeled Analogues of l-Deprenyl for Positron Emission Tomography (PET) studies of Monoamine Oxidase B (MAO-B)

  摘要：

  The aim in this project was to synthesize and to study fluorine-18 labeled analogues of L-deprenyl which bind selectively to the enzyme monoamine oxidase B (MAO-B). Three fluorinated L-deprenyl analogues have been generated in multistep organic syntheses. The most promising fluorine-18 compound N-[(2S)-1-[F-18]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine (4c) was synthesized by a one-step fluorine-18 nucleophilic substitution reaction. Autoradiography on human brain tissue sections demonstrated specific binding for compound 4c to brain regions known to have a high content of MAO-B. In addition, the corresponding nonradioactive fluorine-19 compound (13) inhibited recombinant human MAO-B with an IC50 of 170.5 +/- 29 n/v1 but did not inhibit recombinant human MAO-A (IC50 > 2000 nM), demonstrating its specificity. Biodistribution of 4c in mice showed high initial brain uptake leveling at 5.4 +/- 0.04%ID/g after 2 min post injection. In conclusion, compound 4c is a specific inhibitor of MAO-B with high initial brain uptake in mice and is, therefore, a candidate for further investigation in PET.

  DOI：

  10.1021/jm200710b

文献信息

• [EN] NOVEL PRECURSOR MOLECULES FOR F-18 LABELLED PET TRACERS<br/>[FR] NOUVELLES MOLÉCULES PRÉCURSEURS POUR DES TRACEURS PET MARQUÉS PAR F-18
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2010121719A1

  公开（公告）日：2010-10-28

  This invention relates to novel compounds suitable as precursors for the preparation of certain F-18 labeled positron emission tomography (PET) tracers. Furthermore, the invention relates to the preparation of such precursor molecules and to the preparation of PET tracers by F-18 labeling of such precursors.

  本发明涉及一种新型化合物，适用于制备某些F-18标记的正电子发射断层扫描（PET）示踪剂的前体。此外，本发明还涉及制备这种前体分子和通过对这种前体进行F-18标记制备PET示踪剂的方法。
• COMPOUNDS FOR USE IN IMAGING, DIAGNOSING AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS
  申请人：Lehmann Lutz

  公开号：US20100233086A1

  公开（公告）日：2010-09-16

  This invention relates to novel compounds suitable for labelling or already labelled by 18 F, methods of preparing such a compound, compositions comprising such compounds, kits comprising such compounds or compositions and uses of such compounds, compositions or kits for diagnostic imaging by positron emission tomography (PET).

  本发明涉及适用于标记或已经通过18F标记的新型化合物，制备这种化合物的方法，包含这种化合物的组合物，包含这种化合物或组合物的试剂盒以及这种化合物，组合物或试剂盒用于正电子发射断层摄影（PET）的诊断成像的用途。
• NOVEL PRECURSOR MOLECULES FOR F-18 LABELLED PET TRACERS
  申请人：Kettschau Georg

  公开号：US20120101302A1

  公开（公告）日：2012-04-26

  This invention relates to novel compounds suitable as precursors for the preparation of certain F-18 labeled positron emission tomography (PET) tracers. Furthermore, the invention relates to the preparation of such precursor molecules and to the preparation of PET tracers by F-18 labeling of such precursors.

  本发明涉及一种新型化合物，适用于制备某些F-18标记的正电子发射断层扫描（PET）示踪剂的前体。此外，本发明还涉及制备这种前体分子和通过对这种前体进行F-18标记制备PET示踪剂的方法。
• [EN] COMPOUNDS FOR USE IN IMAGING, DIAGNOSING, AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS<br/>[FR] COMPOSÉS DESTINÉS À ÊTRE UTILISÉS DANS LE CADRE D'IMAGERIE, DE DIAGNOSTIC ET/OU DE TRAITEMENT DE MALADIES DU SYSTÈME NERVEUX CENTRAL OU DE TUMEURS
  申请人：BAYER SCHERING PHARMA AG

  公开号：WO2009052970A3

  公开（公告）日：2009-07-02
• Synthesis of Three Novel Fluorine-18 Labeled Analogues of <scp>l</scp>-Deprenyl for Positron Emission Tomography (PET) studies of Monoamine Oxidase B (MAO-B)
  作者：Sangram Nag、Lutz Lehmann、Tobias Heinrich、Andrea Thiele、Georg Kettschau、Ryuji Nakao、Balázs Gulyás、Christer Halldin

  DOI：10.1021/jm200710b

  日期：2011.10.27

  The aim in this project was to synthesize and to study fluorine-18 labeled analogues of L-deprenyl which bind selectively to the enzyme monoamine oxidase B (MAO-B). Three fluorinated L-deprenyl analogues have been generated in multistep organic syntheses. The most promising fluorine-18 compound N-[(2S)-1-[F-18]fluoro-3-phenylpropan-2-yl]-N-methylprop-2-yn-1-amine (4c) was synthesized by a one-step fluorine-18 nucleophilic substitution reaction. Autoradiography on human brain tissue sections demonstrated specific binding for compound 4c to brain regions known to have a high content of MAO-B. In addition, the corresponding nonradioactive fluorine-19 compound (13) inhibited recombinant human MAO-B with an IC50 of 170.5 +/- 29 n/v1 but did not inhibit recombinant human MAO-A (IC50 > 2000 nM), demonstrating its specificity. Biodistribution of 4c in mice showed high initial brain uptake leveling at 5.4 +/- 0.04%ID/g after 2 min post injection. In conclusion, compound 4c is a specific inhibitor of MAO-B with high initial brain uptake in mice and is, therefore, a candidate for further investigation in PET.