4-羟基哌啶-1-基-((4-苯基乙炔基)苯基)甲酮 | 393110-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-羟基哌啶-1-基-((4-苯基乙炔基)苯基)甲酮
• 英文名称: VU0092273
• 英文别名: (4-hydroxypiperidin-1-yl)-[4-(2-phenylethynyl)phenyl]methanone；(4-Hydroxypiperidin-1-yl)(4-(phenylethynyl)phenyl)methanone
• CAS: 393110-43-5
• 化学式: C₂₀H₁₉NO₂
• mdl: MFCD02642887
• 分子量: 305.376
• InChiKey: FPDBSDNGFNDSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-羟基哌啶 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四(三苯基膦)钯 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-羟基哌啶-1-基-((4-苯基乙炔基)苯基)甲酮
  参考文献：
  名称：

  Development of a novel, CNS-penetrant, metabotropic glutamate receptor 3 (mGlu3) NAM probe (ML289) derived from a closely related mGlu5 PAM

  摘要：

  Herein we report the discovery and SAR of a novel metabotropic glutamate receptor 3 (mGlu(3)) NAM probe (ML289) with 15-fold selectivity versus mGlu(2). The mGlu(3) NAM was discovered via a 'molecular switch' from a closely related, potent mGlu(5) positive allosteric modulator (PAM), VU0092273. This NAM (VU0463597, ML289) displays an IC50 value of 0.66 mu M and is inactive against mGlu(5). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.112

文献信息

• BENZAMIDE mGluR5 POSITIVE ALLOSTERIC MODULATORS AND METHODS OF MAKING AND USING SAME
  申请人：Conn P. Jeffrey

  公开号：US20090042855A1

  公开（公告）日：2009-02-12

  In one aspect, the invention relates to compounds, including phenylethynylbenzamide derivatives, cycloalkylethynylbenzamide derivatives, styrylbenzamide derivatives, 4-(3-phenyl-1,2,4-oxadiazol-5-yl)benzamide derivatives, 4-(pyridinylethynyl)benzamide derivatives, and N 1 -phenylterephthalamide 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.

  本发明涉及化合物，包括苯乙炔基苯甲酰胺衍生物、环烷基乙炔基苯甲酰胺衍生物、苯乙烯基苯甲酰胺衍生物、4-(3-苯基-1,2,4-噁唑-5-基)苯甲酰胺衍生物、4-(吡啶乙炔基)苯甲酰胺衍生物和N1-苯基对苯二甲酰胺衍生物，它们是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；含有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失调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
• US8853392B2
  申请人：——

  公开号：US8853392B2

  公开（公告）日：2014-10-07
• [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.
• Development of a novel, CNS-penetrant, metabotropic glutamate receptor 3 (mGlu3) NAM probe (ML289) derived from a closely related mGlu5 PAM
  作者：Douglas J. Sheffler、Cody J. Wenthur、Joshua A. Bruner、Sheridan J.S. Carrington、Paige N. Vinson、Kiran K. Gogi、Anna L. Blobaum、Ryan D. Morrison、Mitchell Vamos、Nicholas D.P. Cosford、Shaun R. Stauffer、J. Scott Daniels、Colleen M. Niswender、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2012.04.112

  日期：2012.6

  Herein we report the discovery and SAR of a novel metabotropic glutamate receptor 3 (mGlu(3)) NAM probe (ML289) with 15-fold selectivity versus mGlu(2). The mGlu(3) NAM was discovered via a 'molecular switch' from a closely related, potent mGlu(5) positive allosteric modulator (PAM), VU0092273. This NAM (VU0463597, ML289) displays an IC50 value of 0.66 mu M and is inactive against mGlu(5). (C) 2012 Elsevier Ltd. All rights reserved.