2-环戊基-5-羟基-6,7-二甲基-2,3-二氢-1H-茚-1-酮 | 41715-84-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2-环戊基-5-羟基-6,7-二甲基-2,3-二氢-1H-茚-1-酮
• 英文名称: 2-cyclopentyl-5-hydroxy-6,7-dimethyl-indan-1-one
• 英文别名: 2-Cyclopentyl-5-hydroxy-6,7-dimethyl-1-indanon；2-Cyclopentyl-5-hydroxy-6,7-dimethyl-2,3-dihydro-1H-inden-1-one；2-cyclopentyl-5-hydroxy-6,7-dimethyl-2,3-dihydroinden-1-one
• CAS: 41715-84-8
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: KBVHTTPYLFSXBH-UHFFFAOYSA-N

物化性质

• 沸点：
  435.9±45.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  2-环戊基-5-羟基-6,7-二甲基-2,3-二氢-1H-茚-1-酮 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 反应 36.0h， 生成 5-(3-{[(2-cyclopentyl-6,7-dimethyl-1-oxo-2,3-dihydro-1H-inden-5-yl)oxy]methyl}phenyl)nicotinonitrile
  参考文献：
  名称：

  Biphenyl-indanones: Allosteric potentiators of the metabotropic glutamate subtype 2 receptor

  摘要：

  We have identified and synthesized a series of biphenyl-carboxylic acid indanones as allosteric potentiators of the metabotropic glutamate receptor 2. Structure-activity relationship studies directed toward improving the potency and the brain to plasma ratio of the initial lead led to the discovery of 5 and 23 (EC50 = 111 and 5 nM, respectively). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.062
• 作为产物：
  描述：

  环戊乙酸 在 三氯化铝 、 氯化亚砜 、 盐酸二甲胺 、 三溴化硼 作用下， 以 二氯甲烷 、 硫酸 、 溶剂黄146 、 甲苯 为溶剂， 反应 41.0h， 生成 2-环戊基-5-羟基-6,7-二甲基-2,3-二氢-1H-茚-1-酮
  参考文献：
  名称：

  Biphenyl-indanone A, a Positive Allosteric Modulator of the Metabotropic Glutamate Receptor Subtype 2, Has Antipsychotic- and Anxiolytic-Like Effects in Mice

  摘要：

  先前的研究表明，II 类代谢型谷氨酸受体 (mGluR)、mGluR2 和 mGluR3 的激动剂可能为治疗焦虑症和精神分裂症提供一种新方法。然而，mGluR2 和 mGluR3 亚型对 II 组 mGluR 激动剂作用的相对贡献仍不清楚。在本研究中，我们描述了最近报道的 mGluR2 正变构调节剂联苯茚满酮 A (BINA) 的替代合成和进一步药理学表征。在重组系统中，BINA 对 mGluR2 对谷氨酸的反应产生强大且选择性的增强，而对其他 mGluR 亚型的谷氨酸反应没有影响。在海马脑切片中，BINA (1 μM) 显着增强 mGluR2/3 激动剂诱导的内侧穿通通路齿状回突触兴奋性突触传递的抑制。 BINA 在几种预测小鼠抗精神病和抗焦虑样活性的模型中也有效。 BINA 的行为效应被 mGluR2/3 拮抗剂 (2 S )-2-amino-2-[(1 S ,2 S )-2-carboxycycloprop-1-yl]-3-(xanth-9-yl) 阻断) 丙酸 (LY341495)，表明 BINA 的体内作用是由 mGluR2 激活增加介导的。总的来说，这些结果表明 BINA 是一种选择性 mGluR2 正变构调节剂，并为越来越多的证据提供了进一步的支持，即 mGluR2 的选择性变构增强剂模拟 mGluR2/3 激动剂的许多体内作用，这些作用可能预测这些化合物的治疗效用。

  DOI：

  10.1124/jpet.106.102046

文献信息

• [EN] INDANONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] FACTEURS DE POTENTIALISATION D'INDANONE DE RÉCEPTEURS MÉTABOTROPIQUES DE GLUTAMATES
  申请人：MERCK & CO INC

  公开号：WO2006015158A1

  公开（公告）日：2006-02-09

  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.

  本发明涉及一类潜在激活代谢型谷氨酸受体的化合物，包括mGluR2受体，这些化合物在治疗或预防与谷氨酸功能障碍相关的神经系统和精神疾病以及代谢型谷氨酸受体参与的疾病中具有用途。该发明还涉及包含这些化合物的药物组合物以及这些化合物和组合物在预防或治疗代谢型谷氨酸受体参与的疾病中的用途。
• Heterocyclic Indanone Potentiators of Metabotropic Glutamate Receptors
  申请人：Pinkerton B. Anthony

  公开号：US20080096935A1

  公开（公告）日：2008-04-24

  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.

  本发明涉及一种激活型代谢型谷氨酸受体的化合物，包括mGluR2受体，可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在预防或治疗涉及代谢型谷氨酸受体的疾病中使用这些化合物和组合物。
• Indanone Potentiators of Metabotropic Glutamate Receptors
  申请人：Pinkerton Anthony B.

  公开号：US20080312286A1

  公开（公告）日：2008-12-18

  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.

  本发明涉及增强代谢型谷氨酸受体（包括mGluR2受体）的化合物，用于治疗或预防与谷氨酸功能障碍有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在预防或治疗涉及代谢型谷氨酸受体的疾病中使用这些化合物和组合物。
• Allosteric potentiators of the metabotropic glutamate receptor 2 (mGlu2). Part 3: Identification and biological activity of indanone containing mGlu2 receptor potentiators
  作者：Anthony B. Pinkerton、Rowena V. Cube、John H. Hutchinson、Joyce K. James、Michael F. Gardner、Blake A. Rowe、Hervé Schaffhauser、Dana E. Rodriguez、Una C. Campbell、Lorrie P. Daggett、Jean-Michel Vernier

  DOI：10.1016/j.bmcl.2005.01.077

  日期：2005.3

  We have identified and synthesized a series of phenyl-tetrazolyl and 4-thiopyridyl indanones as allosteric potentiators of the metabotropic glutamate receptor 2. Structure activity relationship studies directed toward improving the potency and level of potentiation, as well as PK properties, led to the discovery of 28 (EC50 = 186 nM), which displayed activity in a rodent model for schizophrenia. © 2005 Elsevier Ltd. All rights reserved.
• INDANONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Merck & Co., Inc.

  公开号：EP1773792A1

  公开（公告）日：2007-04-18