3-氰基-N-(6-甲基吡啶-2-基)-4-(萘-1-基)苯甲酰胺 | 1042498-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-氰基-N-(6-甲基吡啶-2-基)-4-(萘-1-基)苯甲酰胺
• 英文名称: 3-cyano-N-(6-methylpyridin-2-yl)-4-(naphthalen-1-yl)benzamide
• 英文别名: 3-Cyano-N-(6-methylpyridin-2-yl)-4-(naphthalen-1-yl)-benzamide；3-cyano-N-(6-methylpyridin-2-yl)-4-naphthalen-1-ylbenzamide
• CAS: 1042498-34-9
• 化学式: C₂₄H₁₇N₃O
• 分子量: 363.418
• InChiKey: YTBWQFAKJAKPCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  65.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氰基-4-三氟甲基磺酰基-N-(6-甲基吡啶-2-基)苯甲酰胺 、 1-萘硼酸 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 水 为溶剂， 以0.2 g的产率得到3-氰基-N-(6-甲基吡啶-2-基)-4-(萘-1-基)苯甲酰胺
  参考文献：
  名称：

  Structure−Activity Relationships Comparing N-(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

  摘要：

  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.

  DOI：

  10.1021/jm900172f

文献信息

• [EN] MODULATORS OF THE METABOTROPIC GLUTAMATE RECEPTOR SUBTYPE 5 AND USES THEREOF<br/>[FR] MODULATEURS DU RÉCEPTEUR MÉTABOTROPIQUE DU GLUTAMATE DE SOUS-TYPE 5 ET LEURS UTILISATIONS
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2008092072A2

  公开（公告）日：2008-07-31

  [EN] Disclosed are compounds and pharmaceutically acceptable salts, which are modulators of the metabotropic glutamate receptor 5, for use in treating drug abuse and other mental disorders, for example, a compound of Formula (I), wherein X, Y, and R¹-R⁴ are as described or a pharmaceutically acceptable salt thereof. Also disclosed are pharmaceutical compositions and methods of use thereof, which involves administering a therapeutically effective amount of a compound or pharmaceutically acceptable salt to a patient.
  [FR] L'invention concerne des composés et des sels pharmaceutiquement acceptables, qui sont des modulateurs du récepteur métabotropique du glutamate de type 5 et sont destinés au traitement d'abus médicamenteux et d'autres troubles mentaux. L'invention concerne, par exemple, un composé de formule (I), dans laquelle X, Y et R¹-R⁴ sont tels que décrits ou un sel pharmaceutiquement acceptable de celui-ci. L'invention porte également sur des compositions pharmaceutiques et sur des méthodes d'utilisation de celles-ci, comprenant l'administration d'une quantité thérapeutiquement efficace d'un composé ou d'un sel pharmaceutiquement acceptable à un patient.
• 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.