PhOH | 664376-59-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: PhOH
• 英文别名: 2-cyclopentyl-1-(2,4-dihydroxy-3-methyl-phenyl)-ethanone；2-cyclopentyl-1-(2,4-dihydroxy-3-methylphenyl)ethanone
• CAS: 664376-59-4
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: ZZBVXYHATOLGKX-UHFFFAOYSA-N

物化性质

• 沸点：
  417.8±15.0 °C(Predicted)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  PhOH 、 methyl 4-(4-bromobutoxy)benzoate 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以0.277 g的产率得到methyl 4-(4-(4-(2-cyclopentylacetyl)-3-hydroxy-2-methylphenoxy)butoxy)benzoate
  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
• 作为产物：
  描述：

  环戊乙酸 在 aluminum (III) chloride 、 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 PhOH
  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

• Acetophenone potentiators of metabotropic glutamate receptors
  申请人：Cube V. Rowena

  公开号：US20050288346A1

  公开（公告）日：2005-12-29

  The present invention is directed to compounds which are potentiators of metabotropic glutamate receptors, including the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved.

  本发明涉及激活型代谢型谷氨酸受体的化合物，包括mGluR2受体，适用于治疗或预防与谷氨酸功能障碍相关的神经和精神障碍以及涉及代谢型谷氨酸受体的疾病。本发明还涉及包含这些化合物的制药组合物以及使用这些化合物和组合物预防或治疗涉及代谢型谷氨酸受体的疾病。
• [EN] ACETOPHENONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] POTENTIALISATEURS ACETOPHENONES DES RECEPTEURS METABOTROPIQUES DU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2004018386A3

  公开（公告）日：2004-11-25
• ACETOPHENONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Merck & Co., Inc.

  公开号：EP1556038A2

  公开（公告）日：2005-07-27
• 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
  作者：Raveendra-Panickar Dhanya、Douglas J. Sheffler、Russell Dahl、Melinda Davis、Pooi San Lee、Li Yang、Hilary Highfield Nickols、Hyekyung P. Cho、Layton H. Smith、Manoranjan S. D’Souza、P. Jeffrey Conn、Andre Der-Avakian、Athina Markou、Nicholas D. P. Cosford

  DOI：10.1021/jm5000563

  日期：2014.5.22

  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.