[2-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl]-methyl-amine | 524717-80-4

• 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-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl]-methyl-amine
• 英文别名: 2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-methylpyridin-4-amine
• CAS: 524717-80-4
• 化学式: C₁₅H₁₇N₃
• 分子量: 239.32
• InChiKey: BHXPHZOOSSXCHR-UHFFFAOYSA-N

物化性质

• 沸点：
  458.1±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [11C]methyl triflate 、 [2-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl]-methyl-amine 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.02h， 生成 2-(3,4-dihydro-1H-isoquinolin-2-yl)-N-methyl-N-(111C)methylpyridin-4-amine
  参考文献：
  名称：

  Radiosynthesis andin vivoevaluation of [¹¹C]Ro-647312: a novel NR1/2B subtype selective NMDA receptor radioligand

  摘要：

  [2-(3,4-二氢-1H-异喹啉-2-基)吡啶-4-基]二甲胺，Ro-647312（1）代表一类新型NR1/2B亚型选择性NMDA配体。Ro-647312已通过从非甲基化合物2制备的[11C]甲基三氟甲磺酸酯与碳-11标记。反应在丙酮中作为溶剂进行，使用水合氢氧化钠作为碱。经过HPLC纯化后，[11C]Ro-647312（[11C]-1）获得了6.9–9.2%（n = 3）的放射化学产率，基于起始的[11C]CO2校正衰减，其特定的放射性在放射合成结束时测定为1.0至3.5 Ci/µmol（37–129 GBq/µmol）。放射化学纯度和化学纯度分别评估为>99%和>95%。在给大鼠静脉注射[11C]-1后，在所有脑结构中放射性分布均匀，与已知的NR2B亚单位分布无关。在整个实验过程中，血浆中的放射性也比任何脑结构都高。[11C]-1不具备使用正电子发射断层扫描成像NMDA受体所需的特性。版权所有 © 2004 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.877
• 作为产物：
  描述：

  2-(3,4-dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl-amine 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 [2-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl]-methyl-amine
  参考文献：
  名称：

  2-(3,4-Dihydro-1H-isoquinolin-2yl)-pyridines as a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  Recently, we disclosed 4-aminoquinolines as structurally novel NR1/2B subtype selective NMDA receptor antagonists. We would now like to report our findings on structurally related pyridine analogues. The SAR developed in this series resulted in the discovery of high affinity antagonists which are selective (vs alpha1 and M1 receptors) and active in vivo. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00007-6

文献信息

• Pyridine substituted isoquinoline derivatives
  申请人：——

  公开号：US20030119870A1

  公开（公告）日：2003-06-26

  The invention relates to compounds of formulae 1 Compounds of the invention have a good affinity to the NMDA receptor and are useful for the treatment of diseases related to this receptor.

  该发明涉及公式1的化合物。该发明的化合物对NMDA受体具有良好的亲和力，并且可用于治疗与该受体相关的疾病。
• PYRIDINE DERIVATIVES AS NMDA RECEPTOR LIGANDS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1448547B1

  公开（公告）日：2005-04-20
• US6831087B2
  申请人：——

  公开号：US6831087B2

  公开（公告）日：2004-12-14
• [EN] PYRIDINE DERIVATIVES AS NMDA RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE PYRIDINE UTILISÉS COMME LIGANDS DU RÉCEPTEUR NMDA
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003040128A1

  公开（公告）日：2003-05-15

  The invention relates to compounds of formulas (IA) or (IB) wherein R1 and R2 are independently from each other hydrogen, lower alkyl, -(CH2)n-OH, -(CH2)n-N(R6)2, -NR6C(O)C(O)O-lower alkyl, -NR6-(CH2)n-OH, -NR6C(O)-lower alkyl, -NH-benzyl or NR6C(O)-(CH2)n-OH; R6 is independently from each other hydrogen or lower alkyl R' is hydrogen or lower alkyl; R3 is hydrogen or amino; R4 is hydrogen or lower alkyl; R5 is hydrogen or halogen; or R1 and R' may be together with the carbon atoms to which they are attached the group (CH2)4-; or R2 and R3 may be together with the carbon atoms to which they are attached the group -N(R6)-CH2-O-CH2-; n is 0, 1, 2 or 3; and to pharmaceutically acceptable acid addition salts thereof. It has been shown that these compounds have a good affinity to the NMDA receptor and they may therefore be used for the treatment of diseases, related to this receptor.
• Radiosynthesis and<i>in vivo</i>evaluation of [¹¹C]Ro-647312: a novel NR1/2B subtype selective NMDA receptor radioligand
  作者：Frédéric Dollé、Héric Valette、Stéphane Demphel、Christine Coulon、Michelle Ottaviani、Michel Bottlaender、Michael Kassiou

  DOI：10.1002/jlcr.877

  日期：2004.11

  [2-(3,4-Dihydro-1H-isoquinolin-2-yl)-pyridin-4-yl]-dimethylamine, Ro-647312 (1) represents a new novel class of NR1/2B subtype selective NMDA ligand. Ro-647312 has been radiolabelled with carbon-11 using [11C]methyl triflate from the nor-methyl compound 2. The reaction was performed in acetone as solvent using aqueous NaOH as base. Following HPLC purification [11C]Ro-647312 ([11C]-1) was obtained in 6.9–9.2% (n = 3) radiochemical yield decay-corrected based on starting [11C]CO2, with specific radioactivity measured at the end of the radiosynthesis ranging from 1.0 to 3.5 Ci/µmol (37–129 GBq/µmol). Radiochemical and chemical purities were assessed as >99 and >95%, respectively. Following i.v. injection of [11C]-1 in rat, the distribution of radioactivity was homogeneous in all brain structures and did not correlate with the known distribution of NR2B subunits. The radioactivity observed in plasma was also higher than any brain structure throughout the time course of the experiment. [11C]-1 does not possess the required properties for imaging NMDA receptors using positron emission tomography. Copyright © 2004 John Wiley & Sons, Ltd.

  [2-(3,4-二氢-1H-异喹啉-2-基)吡啶-4-基]二甲胺，Ro-647312（1）代表一类新型NR1/2B亚型选择性NMDA配体。Ro-647312已通过从非甲基化合物2制备的[11C]甲基三氟甲磺酸酯与碳-11标记。反应在丙酮中作为溶剂进行，使用水合氢氧化钠作为碱。经过HPLC纯化后，[11C]Ro-647312（[11C]-1）获得了6.9–9.2%（n = 3）的放射化学产率，基于起始的[11C]CO2校正衰减，其特定的放射性在放射合成结束时测定为1.0至3.5 Ci/µmol（37–129 GBq/µmol）。放射化学纯度和化学纯度分别评估为>99%和>95%。在给大鼠静脉注射[11C]-1后，在所有脑结构中放射性分布均匀，与已知的NR2B亚单位分布无关。在整个实验过程中，血浆中的放射性也比任何脑结构都高。[11C]-1不具备使用正电子发射断层扫描成像NMDA受体所需的特性。版权所有 © 2004 John Wiley & Sons, Ltd.