n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-dihydro-2Hisoindol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate | 1380347-42-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-dihydro-2Hisoindol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate
• CAS: 1380347-42-1
• 化学式: C₃₂H₄₂N₂O₄S
• 分子量: 550.762
• InChiKey: YWNVBVVIBSDSID-WMTBUUDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  39.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  70.08
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-dihydro-2Hisoindol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate 在 sodium hydroxide 、 盐酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 5.0h， 以65%的产率得到4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-dihydro-2H-isoindol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of γ-lactam analogs of PGE2 as EP4 and EP2/EP4 agonists

  摘要：

  To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl omega-chain moiety of the gamma-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.008
• 作为产物：
  描述：

  methyl [3-(1,3-dihydro-2H-isoindol-2-yl)phenyl]acetate 在 正丁基锂 、 硼烷四氢呋喃络合物 、 sodium hydride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 mineral oil 为溶剂， 反应 7.66h， 生成 n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-dihydro-2Hisoindol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate
  参考文献：
  名称：

  Synthesis and evaluation of γ-lactam analogs of PGE2 as EP4 and EP2/EP4 agonists

  摘要：

  To identify topically effective EP4 agonists and EP2/EP4 dual agonists with excellent subtype selectivity, further optimization of the 16-phenyl omega-chain moiety of the gamma-lactam 5-thia prostaglandin E analog and the 2-mercaptothiazole-4-carboxylic acid analog were undertaken. Rat in vivo evaluation of these newly identified compounds as their poly (lactide-co-glycolide) microsphere formulation, from which sustained release of the test compound is possible, led us to discover compounds that showed efficacy in a rat bone fracture healing model after its topical administration without serious influence on blood pressure and heart rate. A structure-activity relationship study is also presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.008