3-[(6-methylpyridin-2-yl)ethynyl]benzonitrile

• 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: 3-[(6-methylpyridin-2-yl)ethynyl]benzonitrile
• 英文别名: 3-[2-(6-Methylpyridin-2-yl)ethynyl]-benzonitrile；3-[2-(6-methylpyridin-2-yl)ethynyl]benzonitrile
• 化学式: C₁₅H₁₀N₂
• 分子量: 218.258
• InChiKey: FKODYULBKPINFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-溴-6-甲基吡啶 在 四丁基氟化铵 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-[(6-methylpyridin-2-yl)ethynyl]benzonitrile
  参考文献：
  名称：

  有效的mGluR5非竞争性拮抗剂MPEP的苯环3位上的功能化。

  摘要：

  我们描述了在苯环的3位官能化的MPEP类似物的合成和生物学评估。结果指出了在该位置选择官能团的局限性。唯一导致活性保留的取代基是NO（2）（IC（50）= 13 nM）和CN（IC（50）= 8 nM）。

  DOI：

  10.1016/j.bmcl.2004.12.047

文献信息

• Pyridine derivatives
  申请人：Novartis AG

  公开号：US06656957B1

  公开（公告）日：2003-12-02

  A compound of formula I wherein X represents an optionally halo-substituted (C2-4)alkynylene group bonded via vicinal unsaturated carbon atoms.

  化合物I的式子为：X-[(C2-4)炔基]，其中X代表可选卤素取代的通过相邻不饱和碳原子键合的(C2-4)炔基。
• Structure−Activity Relationships Comparing <i>N</i>-(6-Methylpyridin-yl)-Substituted Aryl Amides to 2-Methyl-6-(substituted-arylethynyl)pyridines or 2-Methyl-4-(substituted-arylethynyl)thiazoles as Novel Metabotropic Glutamate Receptor Subtype 5 Antagonists
  作者：Santosh S. Kulkarni、Mu-Fa Zou、Jianjing Cao、Jeffrey R. Deschamps、Alice L. Rodriguez、P. Jeffrey Conn、Amy Hauck Newman

  DOI：10.1021/jm900172f

  日期：2009.6.11

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in anxiety, depression, pain, mental retardation, and addiction. The potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl)pyridine (MPEP, 1) has been a critically important tool used to further elucidate the role of mGluR5 in these CNS disorders. In an effort to provide novel and structurally diverse selective mGluR5 antagonists, we previously described a set of analogues with moderate activity wherein the alkyne bond was replaced with an amide group. In the present report, extended series of both amide and alkyne-based ligands were synthesized. MGluR5 binding and functional data were obtained that identified (1) several novel alkynes with comparable affinities to 1 at mGluR5 (e.g., 10 and 20-23), but (2) most structural variations to the amide template were not well tolerated, although a few potent amides were discovered (e.g., 55 and 56). Several of these novel analogues show drug-like physical properties (e.g., cLogP range = 2-5) that support their use for in vivo investigation into the role of mGluR5 in CNS disorders.
• PYRIDINE DERIVATIVES
  申请人：Novartis AG

  公开号：EP0998459A2

  公开（公告）日：2000-05-10
• US6656957B1
  申请人：——

  公开号：US6656957B1

  公开（公告）日：2003-12-02
• [EN] PYRIDINE DERIVATIVES<br/>[FR] DERIVES DE PYRIDINE
  申请人：——

  公开号：WO1999002497A2

  公开（公告）日：1999-01-21

  [EN] Compounds of the formula (I), wherein X and R1 to R5 are as defined in the description, are useful for treating disorders mediated full or in part by mGluR5.
  [FR] L'invention concerne les composés représentés par la formule (I) dans laquelle X et R1 à R5 sont tels que définis dans le descriptif. Ces composés sont utiles pour traiter les troubles à médiation partielle ou complète de mGluR5.