(R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-benzyloxymethyl-2-pyrrolidinone | 493036-26-3

• 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: (R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-benzyloxymethyl-2-pyrrolidinone
• 英文别名: ethyl 4-[2-[(5R)-2-oxo-5-(phenylmethoxymethyl)pyrrolidin-1-yl]ethyl]benzoate
• CAS: 493036-26-3
• 化学式: C₂₃H₂₇NO₄
• 分子量: 381.472
• InChiKey: OOQUIXGXSKKZSE-OAQYLSRUSA-N

物化性质

• 沸点：
  551.1±40.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-benzyloxymethyl-2-pyrrolidinone 在 palladium-carbon 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 以98%的产率得到(R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-hydroxymethyl-2-pyrrolidinone
  参考文献：
  名称：

  8-Aza-11-deoxy prostaglandin analogues

  摘要：

  本发明涉及一般为EP4受体激动剂的化合物，其表示为式I：其中A为—CH2—CH2—，或—CH═CH—；B为不存在、芳基或杂芳基；R1为烷基、烯烃基、炔烃基、环烷基烷基、杂环烷基烷基、芳基、芳基烷基或杂芳基，当B为芳基或杂芳基且R3、R4、R5和R6不同时为氢时，或者R1为杂环烷基烷基、芳基或杂芳基，当B为不存在且R3、R4、R5和R6同时为氢时；其他取代基如规范中所定义；或其单体异构体、消旋或非消旋异构体混合物，或其药学上可接受的盐或溶剂。该发明还涉及含有此类化合物的药物组合物、用作治疗剂的方法以及其制备方法。

  公开号：

  US20030120079A1
• 作为产物：
  描述：

  (5S)-5-[(benzyloxy)methyl]dihydrofuran-2(3H)-one 在 1,5-二氮杂双环[4.3.0]壬-5-烯 、 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (R)-N'-[2-(4-carboethoxyphenyl)ethyl]-5-benzyloxymethyl-2-pyrrolidinone
  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

• 8-Aza-11-deoxy prostaglandin analogues
  申请人：——

  公开号：US20030120079A1

  公开（公告）日：2003-06-26

  This invention relates to compounds which are generally EP 4 receptor agonists and which are represented by Formula I: 1 wherein A is a —CH 2 —CH 2 —, or —CH═CH—; B is absent, an aryl, or heteroaryl group; R 1 is alkyl, alkenyl, alkynyl, cycloalkylalkyl, heterocyclylalkyl, aryl, arylalkyl or heteroaryl, when B is aryl or heteroaryl and R 3 , R 4 , R 5 and R 6 are not simultaneously hydrogen, or R 1 is heterocyclylalkyl, aryl, or heteroaryl when B is absent and R 3 , R 4 , R 5 and R 6 are simultaneously hydrogen; and the other substituents are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and methods of preparation thereof.

  本发明涉及一般为EP4受体激动剂的化合物，其表示为式I：其中A为—CH2—CH2—，或—CH═CH—；B为不存在、芳基或杂芳基；R1为烷基、烯烃基、炔烃基、环烷基烷基、杂环烷基烷基、芳基、芳基烷基或杂芳基，当B为芳基或杂芳基且R3、R4、R5和R6不同时为氢时，或者R1为杂环烷基烷基、芳基或杂芳基，当B为不存在且R3、R4、R5和R6同时为氢时；其他取代基如规范中所定义；或其单体异构体、消旋或非消旋异构体混合物，或其药学上可接受的盐或溶剂。该发明还涉及含有此类化合物的药物组合物、用作治疗剂的方法以及其制备方法。
• 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.