ethyl (4R,5E,7S)-8-(3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate | 1380347-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl (4R,5E,7S)-8-(3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate
• CAS: 1380347-57-8
• 化学式: C₃₀H₃₈N₂O₆
• 分子量: 522.642
• InChiKey: GYVNMBLEDKBOHD-KVKMCETFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  110.89
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  ethyl (4R,5E,7S)-8-(3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成
  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：

  N-methoxy-N-methyl-2-[3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl]acetamide 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 ethyl (4R,5E,7S)-8-(3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl)-7-hydroxy-4-((tert-butyloxycarbonyl)amino)-5-octenoate
  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