dimethyl [3-(4'-methoxy-3-biphenylyl)-2-oxopropyl]phosphonate | 1380347-09-0

• 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: dimethyl [3-(4'-methoxy-3-biphenylyl)-2-oxopropyl]phosphonate
• CAS: 1380347-09-0
• 化学式: C₁₈H₂₁O₅P
• 分子量: 348.336
• InChiKey: KLWLDTQBLXXRSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  dimethyl [3-(4'-methoxy-3-biphenylyl)-2-oxopropyl]phosphonate 在 硼烷四氢呋喃络合物 、 sodium hydride 、 sodium hydroxide 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 、 mineral oil 为溶剂， 反应 9.66h， 生成 2-[(2-((2R)-2-[(1E,3S)-3-hydroxy-4-(4'-methoxy-1,1'-biphenyl-3-yl)but-1-enyl]-5-oxopyrrolidin-1-yl)ethyl)sulfanyl]-1,3-thiazole-4-carboxylic 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：

  2-(3-bromophenyl)-N-methoxy-N-methylacetamide 在 四(三苯基膦)钯 、 正丁基锂 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 正己烷 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 dimethyl [3-(4'-methoxy-3-biphenylyl)-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