Phosphoric acid 3-bromomethyl-phenyl ester 2-methoxy-3-{6-[2-(2-methoxy-ethoxy)-ethoxy]-hexyloxy}-phenyl ester | 140466-42-8

• 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: Phosphoric acid 3-bromomethyl-phenyl ester 2-methoxy-3-{6-[2-(2-methoxy-ethoxy)-ethoxy]-hexyloxy}-phenyl ester
• CAS: 140466-42-8
• 化学式: C₂₅H₃₆BrO₉P
• 分子量: 591.433
• InChiKey: JUPAWDVCFPPOOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  101.91
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-甲基噻唑 、 Phosphoric acid 3-bromomethyl-phenyl ester 2-methoxy-3-{6-[2-(2-methoxy-ethoxy)-ethoxy]-hexyloxy}-phenyl ester 以 甲苯 为溶剂， 反应 24.0h， 生成 [2-Methoxy-3-[6-[2-(2-methoxyethoxy)ethoxy]hexoxy]phenyl] [3-[(5-methyl-1,3-thiazol-3-ium-3-yl)methyl]phenyl] phosphate
  参考文献：
  名称：

  Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor

  摘要：

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.

  DOI：

  10.1021/jm00087a023
• 作为产物：
  描述：

  2-methoxy-3-[6-[2-(2-methoxyethoxy)ethoxy]hexoxy]phenol 在 sodium acetate 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 为溶剂， 反应 7.5h， 生成 Phosphoric acid 3-bromomethyl-phenyl ester 2-methoxy-3-{6-[2-(2-methoxy-ethoxy)-ethoxy]-hexyloxy}-phenyl ester
  参考文献：
  名称：

  Analogs of platelet activating factor. 6. Mono- and bis-aryl phosphate antagonists of platelet activating factor

  摘要：

  A series of aryl phosphoglyceride (3, 19-6 1) and bis-aryl phosphate (67-135) antagonists of platelet activating factor (PAF) were prepared. A group of four bifunctional phosphorus reagents (5a-c and 7) were developed that allowed the preparation of these aryl phosphates in which the position of aromatic substitution can be varied. These compounds were examined for their ability to inhibit PAF-induced platelet aggregation of rabbit platelets. Selected compounds were also evaluated for their ability to displace [H-3]PAF from its receptor on rabbit platelets. These in vitro data were compared to similar data obtained for a number of known PAF antagonists. The compounds were evaluated in vivo, in both the mouse and rabbit, for their ability to prevent death induced by a lethal challenge of PAF. The relationships between the biological activity and the nature, lipophilicity, and position of substituents of the aromatic rings were studied. Compound 105 (CL 184005) has been selected to undergo further development as a potential therapeutic agent for the treatment of septic shock in man.

  DOI：

  10.1021/jm00087a023