ethyl 7-{(2R)-2-[(1E)-3-oxo-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}heptanoate | 533894-06-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 7-{(2R)-2-[(1E)-3-oxo-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}heptanoate
• 英文别名: ethyl 7-[(5R)-2-oxo-5-[(E)-3-oxo-4-phenylbut-1-enyl]pyrrolidin-1-yl]heptanoate
• CAS: 533894-06-3
• 化学式: C₂₃H₃₁NO₄
• 分子量: 385.503
• InChiKey: FRQUIBIIJSBKMF-GUCAUAJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 7-{(2R)-2-[(1E)-3-oxo-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}heptanoate 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 ethyl 7-[(2R)-2-[(E)-3-hydroxy-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl]heptanoate
  参考文献：
  名称：

  Discovery of a potent and selective agonist of the prostaglandin EP4 receptor

  摘要：

  Analogues of PGE(2) wherein the hydroxycyclopentanone ring has been replaced by a lactam have been prepared and evaluated as ligands for the EP4 receptor. An optimized compound (19a) shows high potency and agonist efficacy at the EP4 receptor and is highly selective over the other seven known prostaglandin receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00042-8
• 作为产物：
  描述：

  7-溴庚酸乙酯 在 sodium hydride 、 戴斯-马丁氧化剂 、 氟化氢吡啶 作用下， 以 乙二醇二甲醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 7-{(2R)-2-[(1E)-3-oxo-4-phenylbut-1-enyl]-5-oxopyrrolidin-1-yl}heptanoate
  参考文献：
  名称：

  Discovery of a potent and selective agonist of the prostaglandin EP4 receptor

  摘要：

  Analogues of PGE(2) wherein the hydroxycyclopentanone ring has been replaced by a lactam have been prepared and evaluated as ligands for the EP4 receptor. An optimized compound (19a) shows high potency and agonist efficacy at the EP4 receptor and is highly selective over the other seven known prostaglandin receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00042-8

文献信息

• Method for treating ocular hypertension
  申请人：——

  公开号：US20040254230A1

  公开（公告）日：2004-12-16

  This invention relates to potent selective agonists of the EP 4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions that are related to elevated intraocular pressure in the eye of a patient. This invention also relates to the use of such compounds to provide a neuroprotective effect to the eye of mammalian species, particularly humans.

  本发明涉及到前列腺素E2受体EP4亚型的有效选择性激动剂，以及它们的使用或制剂在治疗青光眼和其他与患者眼内压升高有关的疾病中。本发明还涉及使用这些化合物为哺乳动物（尤其是人类）的眼提供神经保护作用。
• 8-AZAPROSTAGLANDIN ANALOGS AS AGENTS FOR LOWERING INTRAOCULAR PRESSURE
  申请人：ALLERGAN, INC.

  公开号：EP1503984B1

  公开（公告）日：2013-03-20
• Lactams as EP4 prostanoid receptor subtype selective agonists. Part 1: 2-Pyrrolidinones-stereochemical and lower side-chain optimization
  作者：Todd R. Elworthy、Denis J. Kertesz、Woongki Kim、Michael G. Roepel、Lina Quattrocchio-Setti、David B. Smith、Jahari Laurant Tracy、Audrey Chow、Fujun Li、Emma R. Brill、Leang K. Lach、Daren McGee、Diana S. Yang、San-San Chiou

  DOI：10.1016/j.bmcl.2004.01.063

  日期：2004.4

  A series of 7-[(5R)-substituted 2-oxo-1-pyrrolidinyl]-heptanoic acids were prepared, their isomeric purity determined, and pharmacologically evaluated. Lactams with affinity for the EP4 receptor displayed agonist behavior. The lower side-chain of the lactam template could be substituted to afford ligands (e.g., 17, 24, 30, 31, and 33) of high potency and greater than 1000-fold affinity for EP4 versus the other EP prostanoid receptors. (C) 2004 Elsevier Ltd. All rights reserved.
• Discovery of a potent and selective agonist of the prostaglandin EP4 receptor
  作者：Xavier Billot、Anne Chateauneuf、Nathalie Chauret、Danielle Denis、Gillian Greig、Marie-Claude Mathieu、Kathleen M Metters、Deborah M Slipetz、Robert N Young

  DOI：10.1016/s0960-894x(03)00042-8

  日期：2003.3

  Analogues of PGE(2) wherein the hydroxycyclopentanone ring has been replaced by a lactam have been prepared and evaluated as ligands for the EP4 receptor. An optimized compound (19a) shows high potency and agonist efficacy at the EP4 receptor and is highly selective over the other seven known prostaglandin receptors. (C) 2003 Elsevier Science Ltd. All rights reserved.