6-((2-fluorophenyl)ethynyl)-3,4-dihydroisoquinoline-1(2H)-one | 1092550-60-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 6-((2-fluorophenyl)ethynyl)-3,4-dihydroisoquinoline-1(2H)-one
• 英文别名: 6-((2-fluorophenyl)ethynyl)-3,4-dihydroisoquinolin-1(2H)-one；6-[2-(2-fluorophenyl)ethynyl]-3,4-dihydro-2H-isoquinolin-1-one
• CAS: 1092550-60-1
• 化学式: C₁₇H₁₂FNO
• 分子量: 265.287
• InChiKey: DNVTWDKKJYJBDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-溴-3,4-二氢-2H-异喹啉-1-酮 、 1-乙炔基-2-氟苯 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 生成 6-((2-fluorophenyl)ethynyl)-3,4-dihydroisoquinoline-1(2H)-one
  参考文献：
  名称：

  Synthesis and SAR of centrally active mGlu5 positive allosteric modulators based on an aryl acetylenic bicyclic lactam scaffold

  摘要：

  This Letter describes the hit-to-lead progression and SAR of a series of biphenyl acetylene compounds derived from an HTS screening campaign targeting the mGlu(5) receptor. 'Molecular switches' were identified that modulated modes of pharmacology, and several compounds within this series were shown to be efficacious in reversal of amphetamine induced hyperlocomotion in rats after ip dosing, a preclinical model that shows similar positive effects with known antipsychotic agents. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.01.044

文献信息

• BICYCLIC MGLUR5 POSITIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING SAME
  申请人：Conn P. Jeffrey

  公开号：US20090270362A1

  公开（公告）日：2009-10-29

  In one aspect, the invention relates to bicyclic MGluR5 positive allosteric modulators, for example 6-(phenylethynyl)-3,4-dihydroisoquinolin-1(2H)-one, derivatives thereof, and related compounds, which are useful as positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明涉及双环式MGluR5正向变构调节剂，例如6-(苯乙炔基)-3,4-二氢异喹啉-1(2H)-酮及其衍生物和相关化合物，它们可用作代谢型谷氨酸受体亚型5 (mGluR5)的正向变构调节剂；制备这些化合物的合成方法；包含这些化合物的药物组合物；以及使用这些化合物和组合物治疗与谷氨酸功能障碍相关的神经和精神障碍的方法。本摘要旨在作为搜索特定领域的扫描工具，不限制本发明。
• BENZAMIDE MGLUR5 POSITIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING SAME
  申请人：VANDERBILT UNIVERSITY

  公开号：EP2162136A1

  公开（公告）日：2010-03-17
• US8034806B2
  申请人：——

  公开号：US8034806B2

  公开（公告）日：2011-10-11
• [EN] BENZAMIDE MGLUR5 POSITIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING SAME<br/>[FR] DÉRIVÉS BENZAMIDES MODULATEURS ALLOSTÉRIQUES POSITIFS RÉCEPTEURS MÉTABOTROPIQUES DU GLUTAMATE 5 (MGLUR5) ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：UNIV VANDERBILT

  公开号：WO2008151184A1

  公开（公告）日：2008-12-11

  [EN] In one aspect, the invention relates to compounds, including benzamide derivatives and cyclic benzamide derivatives, which are useful as positive allosteric modulators of the metabotropic glutamate receptor subtype 5 (mGluR5); synthetic methods for making the compounds; pharmaceutical compositions comprising the compounds; and methods of treating neurological and psychiatric disorders associated with glutamate dysfunction using the compounds and compositions. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
  [FR] Selon un aspect, la présente invention concerne des composés, comprenant des dérivés benzamides et des dérivés benzamides cycliques, qui sont utiles en tant que modulateurs positifs allostériques du récepteur de sous-type 5 du glutamate (mGluR5); des procédés synthétiques pour la fabrication des composés; des compositions pharmaceutiques comportant les composés; et des procédés de traitement de troubles neurologiques et psychiatriques associés au dysfonctionnement glutamatergique mettant en uvre les composés et les compositions. Cet abrégé est soumis afin de permettre une recherche générale dans ce domaine précis et ne doit pas être utilisé pour limiter la portée de la présente invention.
• Synthesis and SAR of centrally active mGlu5 positive allosteric modulators based on an aryl acetylenic bicyclic lactam scaffold
  作者：Richard Williams、Jason T. Manka、Alice L. Rodriguez、Paige N. Vinson、Colleen M. Niswender、C. David Weaver、Carrie K. Jones、P. Jeffrey Conn、Craig W. Lindsley、Shaun R. Stauffer

  DOI：10.1016/j.bmcl.2011.01.044

  日期：2011.3

  This Letter describes the hit-to-lead progression and SAR of a series of biphenyl acetylene compounds derived from an HTS screening campaign targeting the mGlu(5) receptor. 'Molecular switches' were identified that modulated modes of pharmacology, and several compounds within this series were shown to be efficacious in reversal of amphetamine induced hyperlocomotion in rats after ip dosing, a preclinical model that shows similar positive effects with known antipsychotic agents. Published by Elsevier Ltd.