n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[1,1'-biphenyl-3-yl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl) thio)butanoate | 1380346-95-1

• 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: n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[1,1'-biphenyl-3-yl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl) thio)butanoate
• CAS: 1380346-95-1
• 化学式: C₃₀H₃₉NO₄S
• 分子量: 509.71
• InChiKey: BBZKYGIVGAIPEM-HUHIARPFSA-N

物化性质

• 沸点：
  683.5±55.0 °C(predicted)
• 密度：
  1.159±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 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：
  0.47
• 拓扑面积：
  66.84
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[1,1'-biphenyl-3-yl]-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57%的产率得到4-[(2-((2R)-2-[(1E,3S)-4-(1,1'-biphenyl-3-yl)-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：

  butyl 4-({2-[(2R)-2-formyl-5-oxo-1-pyrrolidinyl]ethyl}thio)butanoate 在 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 、 甲苯 、 mineral oil 为溶剂， 反应 4.66h， 生成 n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[1,1'-biphenyl-3-yl]-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