3-(2-hydroxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid | 853760-14-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-hydroxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid
• 英文别名: 3-[2-hydroxy-4-[4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy]phenyl]propanoic acid
• CAS: 853760-14-2
• 化学式: C₂₅H₃₂O₇
• 分子量: 444.525
• InChiKey: LLWRMHCFDMBSRE-UHFFFAOYSA-N

物化性质

• 沸点：
  669.6±55.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(2-hydroxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以65%的产率得到7-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}chroman-2-one
  参考文献：
  名称：

  3-(2-Ethoxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid: a brain penetrant allosteric potentiator at the metabotropic glutamate receptor 2 (mGluR2)

  摘要：

  We have identified and synthesized a brain penetrant propanoic acid as an allosteric potentiator of the metabotropic glutamate receptor 2. Structure-activity relationship studies directed toward improving the potency, level of potentiation and brain penetration led to the discovery of 8 (EC50 = 1200 nM, 77% potentiation, 119% brain/plasma in rat, 20 mpk ip, brain level of 5700 nM). © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.078
• 作为产物：
  描述：

  1-(2,4-dihydroxy-3-methylphenyl)-3-methylbutan-1-one 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 3-(2-hydroxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid
  参考文献：
  名称：

  3-(2-Ethoxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid: a brain penetrant allosteric potentiator at the metabotropic glutamate receptor 2 (mGluR2)

  摘要：

  We have identified and synthesized a brain penetrant propanoic acid as an allosteric potentiator of the metabotropic glutamate receptor 2. Structure-activity relationship studies directed toward improving the potency, level of potentiation and brain penetration led to the discovery of 8 (EC50 = 1200 nM, 77% potentiation, 119% brain/plasma in rat, 20 mpk ip, brain level of 5700 nM). © 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.02.078

文献信息

• Heterocyclic Acetophenone Potentiators of Metabotropic Glutamate Receptors
  申请人：Pinkerton Anthony B

  公开号：US20080293684A1

  公开（公告）日：2008-11-27

  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.

  本发明涉及化合物，它们是代谢型谷氨酸受体的增强剂，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代谢型谷氨酸受体参与的疾病。本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方面的使用。
• [EN] HETEROCYCLIC ACETOPHENONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] POTENTIALISATEURS D'ACETOPHENONE HETEROCYCLIQUES DE RECEPTEURS METABOTROPIQUES DU GLUTAMATE
  申请人：MERCK & CO INC

  公开号：WO2006014918A3

  公开（公告）日：2006-06-01
• HETEROCYCLIC ACETOPHENONE POTENTIATORS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Merck & Co., Inc.

  公开号：EP1773774A2

  公开（公告）日：2007-04-18
• 3-(2-Ethoxy-4-{4-[3-hydroxy-2-methyl-4-(3-methylbutanoyl)phenoxy]butoxy}phenyl)propanoic acid: a brain penetrant allosteric potentiator at the metabotropic glutamate receptor 2 (mGluR2)
  作者：Rowena V. Cube、Jean-Michel Vernier、John H. Hutchinson、Michael F. Gardner、Joyce K. James、Blake A. Rowe、Herve Schaffhauser、Lorrie Daggett、Anthony B. Pinkerton

  DOI：10.1016/j.bmcl.2005.02.078

  日期：2005.5

  We have identified and synthesized a brain penetrant propanoic acid as an allosteric potentiator of the metabotropic glutamate receptor 2. Structure-activity relationship studies directed toward improving the potency, level of potentiation and brain penetration led to the discovery of 8 (EC50 = 1200 nM, 77% potentiation, 119% brain/plasma in rat, 20 mpk ip, brain level of 5700 nM). © 2005 Elsevier Ltd. All rights reserved.