3-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)-butoxy)-4-methoxybenzoic acid | 1609477-33-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)-butoxy)-4-methoxybenzoic acid
• 英文别名: 3-(4-(4-(3,3-Dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)butoxy)-4-methoxybenzoic acid；3-[4-[4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy]butoxy]-4-methoxybenzoic acid
• CAS: 1609477-33-9
• 化学式: C₂₅H₃₂O₇
• 分子量: 444.525
• InChiKey: AOYJKNKRKBOUAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)-butoxy)-4-methoxybenzoic acid 、 盐酸甲胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以59%的产率得到3-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)butoxy)-4-methoxy-N-methylbenzamide
  参考文献：
  名称：

  [EN] METABOTROPIC GLUTAMATE RECEPTOR POSITIVE ALLOSTERIC MODULATORS (PAMS) AND USES THEREOF
  [FR] MODULATEURS ALLOSTÉRIQUES POSITIFS (PAM) DU RÉCEPTEUR MÉTABOTROPIQUE DU GLUTAMATE ET LEURS UTILISATIONS

  摘要：

  本文件提供了小分子活性的代谢型谷氨酸亚型-2和-3受体正变构调节剂（PAMS），包括这些化合物的组合物，以及使用这些化合物和包含这些化合物的组合物的方法。

  公开号：

  WO2015157187A1
• 作为产物：
  描述：

  3,3-二甲基-1-丁酸 在 aluminum (III) chloride 、 草酰氯 、 potassium carbonate 、 potassium iodide 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 24.25h， 生成 3-(4-(4-(3,3-dimethylbutanoyl)-3-hydroxy-2-methylphenoxy)-butoxy)-4-methoxybenzoic acid
  参考文献：
  名称：

  Design and Synthesis of Systemically Active Metabotropic Glutamate Subtype-2 and -3 (mGlu_2/3) Receptor Positive Allosteric Modulators (PAMs): Pharmacological Characterization and Assessment in a Rat Model of Cocaine Dependence

  摘要：

  As part of our ongoing small-molecule metabotropic glutamate (mGlu) receptor positive allosteric modulator (PAM) research, we performed structure activity relationship (SAR) studies around a series of group II mGlu PAMs. Initial analogues exhibited weak activity as mGlu(2) receptor PAMs and no activity at mGlu(3). Compound optimization led to the identification of potent mGlu(2/3) selective PAMs with no in vitro activity at mGlu(1,4-8) or 45 other CNS receptors. In vitro pharmacological characterization of representative compound 44 indicated agonist-PAM activity toward mGlu(2) and PAM activity at mGlu(3). The most potent mGlu(2/3) PAMs were characterized in assays predictive of ADME/T and pharmacokinetic (PK) properties, allowing the discovery of systemically active mGlu(2/3) PAMs. On the basis of its overall profile, compound 74 was selected for behavioral studies and was shown to dose-dependently decrease cocaine self-administration in rats after intraperitoneal administration. These mGlu(2/3) receptor PAMs have significant potential as small molecule tools for investigating group II mGlu pharmacology.

  DOI：

  10.1021/jm5000563

文献信息

• Metabotropic glutamate receptor positive allosteric modulators (PAMS) and uses thereof
  申请人：Sanford-Burnham Medical Research Institute

  公开号：US10099993B2

  公开（公告）日：2018-10-16

  Provided herein are small molecule active metabotropic glutamate subtype-2 and -3 receptor positive allosteric modulators (PAMS), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  本文提供了小分子活性代谢型谷氨酸亚型-2 和-3 受体正异位调节剂（PAMS）、包含这些化合物的组合物以及使用这些化合物和包含这些化合物的组合物的方法。
• METABOTROPIC GLUTAMATE RECEPTOR POSITIVE ALLOSTERIC MODULATORS (PAMS) AND USES THEREOF
  申请人：Sanford-Burnham Medical Research Institute

  公开号：EP3129345A1

  公开（公告）日：2017-02-15
• Metabotropic Glutamate Receptor Positive Allosteric Modulators (PAMS) and Uses Thereof
  申请人：Sanford-Burnham Medical Research Institute

  公开号：US20170036987A1

  公开（公告）日：2017-02-09

  Provided herein are small molecule active metabotropic glutamate subtype-2 and -3 receptor positive allosteric modulators (PAMS), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.