(13E)-9,15-dioxo-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester | 729611-32-9

• 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: (13E)-9,15-dioxo-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester
• CAS: 729611-32-9
• 化学式: C₂₉H₃₅NO₅S
• 分子量: 509.667
• InChiKey: XGFSXAPKYJXVTJ-BOMYWPOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  36.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (13E)-9,15-dioxo-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester 在 硼烷四氢呋喃络合物 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 甲苯 为溶剂， 反应 1.08h， 生成 (15α,13E)-9-oxo-15-hydroxy-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester
  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
• 作为产物：
  描述：

  butyl 4-({2-[(4S)-4-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]ethyl}thio)butanoate 在 三氧化硫吡啶 、 sodium hydride 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 mineral oil 为溶剂， 反应 2.33h， 生成 (13E)-9,15-dioxo-16-(3-phenylphenyl)-17,18,19,20-tetranol-5-thia-8-aza-10-oxaprost-13-enoic acid-n-butylester
  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

• 8-AZAPROSTAGLANDIN DERIVATIVES AND MEDICINAL USES THEREOF
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：EP1586564B1

  公开（公告）日：2012-11-28