ethyl 4-[2-[(2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate | 493036-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 4-[2-[(2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate
• CAS: 493036-28-5
• 化学式: C₂₃H₃₃NO₄
• 分子量: 387.519
• InChiKey: PQERHHXUPMYDTO-WIUNFGAVSA-N

物化性质

• 沸点：
  559.6±50.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-[2-[(2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of N-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents

  摘要：

  Two distinct synthetic schemes were applied to access heteroatom-containing alpha-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. gamma-Lactams were characterized for their prostanoid EP receptor affinities and EP4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.

  DOI：

  10.1021/jm049290a
• 作为产物：
  描述：

  (5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one 在 palladium on activated charcoal dimethyl sulfide borane 、 1,5-二氮杂双环[4.3.0]壬-5-烯 、 potassium tert-butylate 、 氢气 、 对甲苯磺酸 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium chloride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 0.42h， 生成 ethyl 4-[2-[(2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl]ethyl]benzoate
  参考文献：
  名称：

  Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of N-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents

  摘要：

  Two distinct synthetic schemes were applied to access heteroatom-containing alpha-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. gamma-Lactams were characterized for their prostanoid EP receptor affinities and EP4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.

  DOI：

  10.1021/jm049290a

文献信息

• PROSTAGLANDIN ANALOGUES-AS EP4 RECEPTOR AGONISTS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1409455A1

  公开（公告）日：2004-04-21
• [EN] PROSTAGLANDIN ANALOGUES_AS EP4 RECEPTOR AGONISTS<br/>[FR] ANALOGUES DE LA PROSTAGLANDINE UTILISES COMME AGONISTES DU RECEPTEUR EP4
  申请人：HOFFMANN LA ROCHE

  公开号：WO2003008377A1

  公开（公告）日：2003-01-30

  This invention relates to compounds according to Formula I or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof, wherein A, B, R1 to R6 and Z are defined as in claim I. The invention further relates to pharmaceutical compositions comprising such compounds, the use of these compounds as therapeutic agents, and methods of preparation these compounds.
• Lactams as EP₄ Prostanoid Receptor Agonists. 3. Discovery of <i>N</i>-Ethylbenzoic Acid 2-Pyrrolidinones as Subtype Selective Agents
  作者：Todd R. Elworthy、Emma R. Brill、San-San Chiou、Frances Chu、Jason R. Harris、R. Than Hendricks、Jane Huang、Woongki Kim、Leang K. Lach、Tara Mirzadegan、Calvin Yee、Keith A. M. Walker

  DOI：10.1021/jm049290a

  日期：2004.12.1

  Two distinct synthetic schemes were applied to access heteroatom-containing alpha-chain lactams or lactams terminated as aryl acids. The latter lactams were devised using a pharmacophore for EP4 receptor activity. gamma-Lactams were characterized for their prostanoid EP receptor affinities and EP4 activity and found to be selective for the EP2 and EP4 receptors or selective for the EP4 subtype. Benzoic acid 17 displayed enhanced in vivo exposure relative to 3.