5-(2-methylquinolin-7-yl)nicotinonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(2-methylquinolin-7-yl)nicotinonitrile
• 英文别名: 5-(2-methylquinolin-7-yl)pyridine-3-carbonitrile
• 化学式: C₁₆H₁₁N₃
• 分子量: 245.283
• InChiKey: AYJCNPHACWMDIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(2-methylquinolin-7-yl)nicotinonitrile 在 氢溴酸 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 5-(2-methylquinolin-7-yl)nicotinonitrile dihydrobromide
  参考文献：
  名称：

  Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

  摘要：

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl) pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC(50) range 60-100 nM) in the quinoline series. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.03.053
• 作为产物：
  描述：

  2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline 、 5-溴烟腈 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 0.5h， 以80%的产率得到5-(2-methylquinolin-7-yl)nicotinonitrile
  参考文献：
  名称：

  Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

  摘要：

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl) pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC(50) range 60-100 nM) in the quinoline series. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.03.053

文献信息

• Rational design of 7-arylquinolines as non-competitive metabotropic glutamate receptor subtype 5 antagonists
  作者：Jared B.J. Milbank、Christopher S. Knauer、Corinne E. Augelli-Szafran、Annette T. Sakkab-Tan、Kristin K. Lin、Koji Yamagata、Jennifer K. Hoffman、Nian Zhuang、John Thomas、Paul Galatsis、John A. Wendt、John W. Mickelson、Roy D. Schwarz、Jack J. Kinsora、Susan M. Lotarski、Korana Stakich、Kristen K. Gillespie、Wing W. Lam、Abdul E. Mutlib

  DOI：10.1016/j.bmcl.2007.06.030

  日期：2007.8

  Rational replacement of the alkyne linker of mGluR5 antagonist MPEP gave 7-arylquinolines. SAR optimization gave an orally active compound with high affinity for the MPEP binding site. (c) 2007 Elsevier Ltd. All rights reserved.
• Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5
  作者：Peng Zhang、Mu-Fa Zou、Alice L. Rodriguez、P. Jeffrey Conn、Amy Hauck Newman

  DOI：10.1016/j.bmc.2010.03.053

  日期：2010.5

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl) pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC(50) range 60-100 nM) in the quinoline series. Published by Elsevier Ltd.