7-{(2R)-2-[(1E,3S)-4-(3-fluorophenyl)-3-hydroxybut-1-enyl]-5-thioxopyrrolidin-1-yl}heptanoic acid | 729611-99-8

• 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: 7-{(2R)-2-[(1E,3S)-4-(3-fluorophenyl)-3-hydroxybut-1-enyl]-5-thioxopyrrolidin-1-yl}heptanoic acid
• 英文别名: 7-{(2R)-2-[(1E,3S)-4-(3-fluorophenyl)-3-hydroxybut-1-enyl]-5-thioxopyrrolidine-1-yl}heptanoic acid；7-[(2R)-2-[(E,3S)-4-(3-fluorophenyl)-3-hydroxybut-1-enyl]-5-sulfanylidenepyrrolidin-1-yl]heptanoic acid
• CAS: 729611-99-8
• 化学式: C₂₁H₂₈FNO₃S
• 分子量: 393.523
• InChiKey: XIYJUZDXEOVVOG-AYLUNBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  C₂₅H₃₄FNO₃S 在 硼烷四氢呋喃络合物 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 乙二醇二甲醚 、 乙醇 、 甲苯 为溶剂， 反应 17.08h， 生成 7-{(2R)-2-[(1E,3S)-4-(3-fluorophenyl)-3-hydroxybut-1-enyl]-5-thioxopyrrolidin-1-yl}heptanoic 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.