3-[4-[(diethoxyphosphinyl)oxy]phenyl]-4-oxo-4H-1-benzopyran-5,7-diyl phosphoric acid tetraethyl ester | 1453477-50-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-[4-[(diethoxyphosphinyl)oxy]phenyl]-4-oxo-4H-1-benzopyran-5,7-diyl phosphoric acid tetraethyl ester
• CAS: 1453477-50-3
• 化学式: C₂₇H₃₇O₁₄P₃
• 分子量: 678.504
• InChiKey: NLHLGWRZQUXKGL-UHFFFAOYSA-N

物化性质

• 沸点：
  664.7±55.0 °C(predicted)
• 密度：
  1.329±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.14
• 重原子数：
  44.0
• 可旋转键数：
  19.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  164.49
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  染料木素 、 氯磷酸二乙酯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以73%的产率得到3-[4-[(diethoxyphosphinyl)oxy]phenyl]-4-oxo-4H-1-benzopyran-5,7-diyl phosphoric acid tetraethyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of phosphorylated flavonoids as potent and selective inhibitors of cholesterol esterase

  摘要：

  A series of phosphorylated flavonoids were synthesized and investigated in vitro as inhibitors of pancreatic cholesterol esterase (CEase) and acetylcholinesterase (AChE). The results showed that most of the synthesized compounds exhibited nanomolar potency against CEase, much better than the parent flavonoids. Furthermore, these phosphorylated flavonoids demonstrated good to high selectivity for CEase over AChE, which only showed micromolar potency inhibition of AChE. The most selective and potent inhibitor of CEase (3e) had IC50 value of 0.72 nM and 11800-fold selectivity for CEase over AChE. The structure activity relationships revealed that the free hydroxyl group at position 5 and phosphate group at position 7 of the phosphorylated flavonoids are favorable to the inhibition of CEase. The inhibition mechanism and kinetic characterization studies indicated that they are irreversible competitive inhibitors of CEase. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.025