4-oxo-2-phenyl-4H-1-benzopyran-6-yl phosphoric acid dimethyl ester | 1453477-48-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-oxo-2-phenyl-4H-1-benzopyran-6-yl phosphoric acid dimethyl ester
• CAS: 1453477-48-9
• 化学式: C₁₇H₁₅O₆P
• 分子量: 346.276
• InChiKey: DQGWNHYGZDXACC-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87 °C
• 沸点：
  459.2±45.0 °C(predicted)
• 密度：
  1.349±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.97
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  6-羟基黄酮 、 亚磷酸二甲酯 在 四氯化碳 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以54%的产率得到4-oxo-2-phenyl-4H-1-benzopyran-6-yl phosphoric acid dimethyl 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