2-pyridin-4-yl-1,2,3,4-tetrahydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 2-pyridin-4-yl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-Pyridin-4-yl-1,2,3,4-tetrahydro-isoquinoline；2-pyridin-4-yl-3,4-dihydro-1H-isoquinoline
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: CIOBWNSCGKJAQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-pyridin-4-yl-1,2,3,4-tetrahydroisoquinoline 、 间二溴苄 以 丁酮 为溶剂， 以69%的产率得到1,1'-[1,3-phenylenebis(methylene)]bis[4-(3,4-dihydroisoquinolin-2(1H)-yl)pyridinium] dibromide
  参考文献：
  名称：

  同型双季杂环杂环铵盐作为有效的乙酰基和丁酰胆碱酯酶抑制剂：系统的研究的连接和阳离子头对亲和力和选择性的影响。

  摘要：

  季铵盐（QASs）的分子库，主要由具有胆碱激酶（ChoK）抑制活性的对称双季铵溴化物组成，评估了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力（分别为AChE和BChE）。QAS的分子框架由两个带正电荷的杂芳族（吡啶或喹啉鎓）或空间受阻的脂肪族（喹啉鎓）氮环通过亲脂性刚性或半刚性接头保持适当的距离组成。许多同二聚体QAS在纳摩尔范围内显示出AChE和BChE抑制能力，并且酶选择性低。关于AChE，BChE，56）表现出最高的AChE亲和力（IC 50 = 15 nM）和选择性超过BChE和ChoK（分别为SI = 50和562），并且在重症肌无力和神经肌肉阻滞中有希望的药理潜力。

  DOI：

  10.1021/jm101299d
• 作为产物：
  描述：

  4-氯吡啶 、 四氢异喹啉 在 sodium hydroxide 作用下， 以 水 为溶剂， 以88%的产率得到2-pyridin-4-yl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Pyridine substituted isoquinoline derivatives

  摘要：

  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。

  公开号：

  US20030119870A1

文献信息

• Visible-light-induced direct α-C(sp 3 )–H thiocyanation of tertiary amines
  作者：Arvind K. Yadav、Lal Dhar S. Yadav

  DOI：10.1016/j.tetlet.2015.10.048

  日期：2015.12

  eosin Y catalyzed aerobic oxidative α-C(sp3)–H thiocyanation of tertiary amines is reported. The reaction proceeds through visible-light-induced in situ generation of the iminium ion followed by attack of −SCN nucleophile. This is the first example of visible-light-initiated formation of C(sp3)–S bond employing organo-photoredox catalysis. Mild reaction conditions and use of air and visible light as the

  可见光诱导的曙红Y催化叔胺的需氧氧化α-C（sp 3）–H硫氰化。该反应通过可见光诱导的原位生成亚胺离子，随后的攻击- SCN亲核体。这是利用有机光氧化还原催化可见光引发的C（sp 3）-S键形成的第一个例子。该方案的主要特点是温和的反应条件以及在室温下使用空气和可见光作为最绿色和可持续的试剂。
• 4-(3,4-Dihydro-1H-isoquinolin-2yl)-pyridines and 4-(3,4-Dihydro-1H-isoquinolin-2-yl)-quinolines as potent NR1/2B subtype selective NMDA receptor antagonists
  作者：Bernd Büttelmann、Alexander Alanine、Anne Bourson、Ramanjit Gill、Marie-Paule Heitz、Vincent Mutel、Emmanuel Pinard、Gerhard Trube、René Wyler

  DOI：10.1016/s0960-894x(03)00232-4

  日期：2003.5

  A series of 4-(3,4-dihydro-1H-isoquinolin-2yl)-pyridines and analogous quinolines was prepared and evaluated as NR1/2B subtype selective NMDA receptor antagonists. 2-Hydroxyalkylamino substitution combines high affinity with selectivity (vs alpha1 and M1 receptors) and activity in vivo. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Are We There Yet? Applying Thermodynamic and Kinetic Profiling on Embryonic Ectoderm Development (EED) Hit-to-Lead Program
  作者：Ying Wang、Rohinton P. Edalji、Sanjay C. Panchal、Chaohong Sun、Stevan W. Djuric、Anil Vasudevan

  DOI：10.1021/acs.jmedchem.7b00576

  日期：2017.10.26

  It is advocated that kinetic and thermodynamic profiling of bioactive compounds should be incorporated and utilized as complementary tools for hit and lead optimizations in drug discovery. To assess their applications in the EED hit-to-lead optimization process, large amount of thermodynamic and kinetic data were collected and analyzed via isothermal titration calorimetry (ITC) and surface plasmon resonance (SPR), respectively. Slower dissociation rates (k(off)) of the lead compounds were observed as the program progressed. Analysis of the kinetic data indicated that compound cellular activity correlated with both K-i; and k(off). Our analysis revealed that ITC data should be interpreted in the context of chiral purity of the compounds. The thermodynamic signatures of the EED aminopyrrolidine compounds were found to be mainly enthalpy driven with improved enthalpic contributions as the program progressed. Our study also demonstrated that significant challenges still exist in utilizing kinetic and thermodynamic parameters for hit selection.
• 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