2-{[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amino}ethanol | 1146973-03-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-{[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amino}ethanol
• 英文别名: 2-[[(2R)-1-phenylpropan-2-yl]-prop-2-ynylamino]ethanol
• CAS: 1146973-03-6
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: XJKUSPIAHHMSAI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-{[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amino}ethanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到N-(2-chloroethyl)-N-[(2R)-1-phenylpropan-2-yl]prop-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
• 作为产物：
  描述：

  R-（-）-去甲基去异戊烯基盐酸盐 、 2-溴乙醇 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以86%的产率得到2-{[(2R)-1-phenylpropan-2-yl](prop-2-yn-1-yl)amino}ethanol
  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

• 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。
• 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：US08784775B2

  公开（公告）日：2014-07-22

  This invention relates to novel compounds suitable for labeling or already labeled by 18F, 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).

  本发明涉及一种新型化合物，适用于标记或已经用18F标记，制备此类化合物的方法，包含此类化合物的组合物，包含此类化合物或组合物的工具箱以及此类化合物、组合物或工具箱用于正电子发射断层摄影（PET）诊断成像的用途。
• [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
• COMPOUNDS FOR USE IN IMAGING, DIAGNOSING, AND/OR TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM OR OF TUMORS
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP2217549A2

  公开（公告）日：2010-08-18
• US8784775B2
  申请人：——

  公开号：US8784775B2

  公开（公告）日：2014-07-22