4-(4-(phosphonooxy)benzoyl)phenyl hexanoate

• 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: 4-(4-(phosphonooxy)benzoyl)phenyl hexanoate
• 英文别名: [4-(4-Phosphonooxybenzoyl)phenyl] hexanoate
• 化学式: C₁₉H₂₁O₇P
• 分子量: 392.345
• InChiKey: GNSCIIGRQSTTSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4,4'-二羟基二苯甲酮 在 吡啶 、 四氮唑 、 盐酸 、 双氧水 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 4-(4-(phosphonooxy)benzoyl)phenyl hexanoate
  参考文献：
  名称：

  Structure−Activity Relationships of Lysophosphatidic Acid:  Conformationally Restricted Backbone Mimetics

  摘要：

  Lysophosphatidic acid (LPA) has associated with it an intriguing cell biology that is thought to be mediated through its interaction with G-protein coupled receptor(s). In an effort to extend the structure-activity relationships of LPA, we have produced a series of LPA analogues in which the glycerol core in LPA was replaced with conformationally restricted aryl substructures. The aryl substructures encompassed aminophenol, resorcinol, dihydroxy benzophenone, and tocopherol systems. The benzophenone moiety was investigated both as a conformationally restricting substructure for LPA and as a possible photoreactive alkylating agent for the LPA receptor(s). All LPA analogues were evaluated for their potency and efficacy in mobilizing calcium ions from internal stores in MDA MB-231 cells. Ten of the 14 analogues exhibited activity in this assay at doses up to 5 mu M; none of the compounds exhibited nonreceptor-mediated lytic activity at this maximal concentration. The receptor response showed surprising tolerance for manipulation in the backbone region of LPA, although none of the compounds were equipotent to LPA. This tolerance for a variety of structures has given us new leads into the realization of novel agonists and antagonists of the LPA receptor(s).

  DOI：

  10.1021/jm970809v

文献信息

• Structure−Activity Relationships of Lysophosphatidic Acid:  Conformationally Restricted Backbone Mimetics
  作者：Darrin W. Hopper、Seamus P. Ragan、Shelley B. Hooks、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1021/jm970809v

  日期：1999.3.1

  Lysophosphatidic acid (LPA) has associated with it an intriguing cell biology that is thought to be mediated through its interaction with G-protein coupled receptor(s). In an effort to extend the structure-activity relationships of LPA, we have produced a series of LPA analogues in which the glycerol core in LPA was replaced with conformationally restricted aryl substructures. The aryl substructures encompassed aminophenol, resorcinol, dihydroxy benzophenone, and tocopherol systems. The benzophenone moiety was investigated both as a conformationally restricting substructure for LPA and as a possible photoreactive alkylating agent for the LPA receptor(s). All LPA analogues were evaluated for their potency and efficacy in mobilizing calcium ions from internal stores in MDA MB-231 cells. Ten of the 14 analogues exhibited activity in this assay at doses up to 5 mu M; none of the compounds exhibited nonreceptor-mediated lytic activity at this maximal concentration. The receptor response showed surprising tolerance for manipulation in the backbone region of LPA, although none of the compounds were equipotent to LPA. This tolerance for a variety of structures has given us new leads into the realization of novel agonists and antagonists of the LPA receptor(s).