4-[(2-{(4S)-4-[(1E,3S)-3-hydroxy-4-phenylbut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid | 729611-46-5

• 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: 4-[(2-{(4S)-4-[(1E,3S)-3-hydroxy-4-phenylbut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid
• 英文别名: (15α,13E)-9-oxo-15-hydroxy-16-phenyl-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid；4-[2-[(4S)-4-[(E,3S)-3-hydroxy-4-phenylbut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl]ethylsulfanyl]butanoic acid
• CAS: 729611-46-5
• 化学式: C₁₉H₂₅NO₅S
• 分子量: 379.477
• InChiKey: NDXHKZREOPRWCR-IBHATUTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  S-(2-{(4S)-4-[(benzyloxy)methyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl) ethanethioate 在 硼烷四氢呋喃络合物 、 茴香硫醚 、 potassium tert-butylate 、 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 31.41h， 生成 4-[(2-{(4S)-4-[(1E,3S)-3-hydroxy-4-phenylbut-1-enyl]-2-oxo-1,3-oxazolidin-3-yl}ethyl)sulfanyl]butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists

  摘要：

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.009

文献信息

• Synthesis and evaluation of novel modified γ-lactam prostanoids as EP4 subtype-selective agonists
  作者：Tohru Kambe、Toru Maruyama、Toshihiko Nagase、Seiji Ogawa、Chiaki Minamoto、Kiyoto Sakata、Takayuki Maruyama、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2011.12.009

  日期：2012.1

  To identify chemically and metabolically stable subtype-selective EP4 agonists, design and synthesis of a series of modified gamma-lactam prostanoids has been continued. Prostanoids bearing 2-oxo-1,3-oxazolidine, 2-oxo-1,3-thiazolidine and 5-thioxopyrrolidine as a surrogate for the gamma-hydroxycyclopentanone without a troublesome 11-hydroxy group were identified as highly subtype-selective EP4 agonists. Among the tested, several representative compounds demonstrated in vivo efficacy after oral dosing in rats. Their pharmacokinetic and structure-activity relationship studies are presented. (C) 2011 Elsevier Ltd. All rights reserved.