dimethyl (3-[3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl]-2-oxopropyl)phosphonate | 1380347-19-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl (3-[3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl]-2-oxopropyl)phosphonate
• CAS: 1380347-19-2
• 化学式: C₂₀H₂₂NO₅P
• 分子量: 387.372
• InChiKey: GKAIMVXPPTZCHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  78.63
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl (3-[3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl]-2-oxopropyl)phosphonate 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 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
• 作为产物：
  描述：

  在 正丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 9.0h， 生成 dimethyl (3-[3-(5,7-dimethyl-1,3-benzoxazol-2-yl)phenyl]-2-oxopropyl)phosphonate
  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