butyl 4-[(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)but-1-enyl]-5-thioxopyrrolidin-1-yl}ethyl)sulfanyl]butanoate | 1357177-80-0

• 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: butyl 4-[(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)but-1-enyl]-5-thioxopyrrolidin-1-yl}ethyl)sulfanyl]butanoate
• 英文别名: (15α,13E)-9-thioxo-15-t-butyldimethylsilyloxy-16-(3-methylphenyl)-17,18,19,20-tetranor-5-thia-8-azaprost-13-enoic acid butyl ester；butyl 4-[2-[(2R)-2-[(E,3S)-3-[tert-butyl(dimethyl)silyl]oxy-4-(3-methylphenyl)but-1-enyl]-5-sulfanylidenepyrrolidin-1-yl]ethylsulfanyl]butanoate
• CAS: 1357177-80-0
• 化学式: C₃₁H₅₁NO₃S₂Si
• 分子量: 577.968
• InChiKey: GMVOVCDTZSZIED-DXIRENTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.13
• 重原子数：
  38
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  96.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  butyl 4-[(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)but-1-enyl]-5-thioxopyrrolidin-1-yl}ethyl)sulfanyl]butanoate 在 四丁基氟化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 33.0h， 生成 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxy-4-(3-methylphenyl)but-1-enyl]-5-thioxopyrrolidin-1-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
• 作为产物：
  描述：

  (15α,13E)-9-oxo-15-t-butyldimethylsilyloxy-16-(3-methylphenyl)-17,18,19,20-tetranor-5-thia-8-azaprost-13-enoic acid butyl ester 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 butyl 4-[(2-{(2R)-2-[(1E,3S)-3-(tert-butyldimethylsilyloxy)-4-(3-methylphenyl)but-1-enyl]-5-thioxopyrrolidin-1-yl}ethyl)sulfanyl]butanoate
  参考文献：
  名称：

  REMEDIES FOR DISEASES WITH BONE MASS LOSS HAVING EP4 AGONIST AS THE ACTIVE INGREDIENT

  摘要：

  公开号：

  EP1417975B1