diethyl flavon-6-yl phosphate | 1294512-63-2

• 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: diethyl flavon-6-yl phosphate
• 英文别名: Diethyl (4-oxo-2-phenyl-4H-chromen-6-yl) phosphate；diethyl (4-oxo-2-phenylchromen-6-yl) phosphate
• CAS: 1294512-63-2
• 化学式: C₁₉H₁₉O₆P
• 分子量: 374.33
• InChiKey: MDOJEACSAMCINM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-羟基黄酮 、 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 24.5h， 以74%的产率得到diethyl flavon-6-yl phosphate
  参考文献：
  名称：

  A new synthesis of fully phosphorylated flavones as potent pancreatic cholesterol esterase inhibitors

  摘要：

  五种含有一到四个酚羟基的黄酮被完全磷酸化，得到了效果很好、对胰胆固醇酯酶（CEase）有抑制作用的化合物，其IC50值在纳摩尔范围内，比原来的化合物强很多。抑制机制和动力学特性研究表明它们是不可逆的竞争性抑制剂。

  DOI：

  10.1039/c0ob00640h

文献信息

• Synthesis and biological evaluation of phosphorylated flavonoids as potent and selective inhibitors of cholesterol esterase
  作者：Yingling Wei、Ai-Yun Peng、Bo Wang、Lin Ma、Guoping Peng、Yidan Du、Jingming Tang

  DOI：10.1016/j.ejmech.2013.03.025

  日期：2014.3

  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.
• A new synthesis of fully phosphorylated flavones as potent pancreatic cholesterol esterase inhibitors
  作者：Guoping Peng、Yidan Du、Yingling Wei、Jingming Tang、Ai-Yun Peng、Liqun Rao

  DOI：10.1039/c0ob00640h

  日期：——

  Five flavones possessing one to four phenolic groups were fully phosphorylated efficiently and the obtained compounds showed excellent pancreatic cholesterol esterase (CEase) inhibitory activities with IC50 in the nanomolar range, which were much more potent than their parent compounds. The inhibition mechanism and kinetic characterization studies indicate that they are irreversible competitive inhibitors.

  五种含有一到四个酚羟基的黄酮被完全磷酸化，得到了效果很好、对胰胆固醇酯酶（CEase）有抑制作用的化合物，其IC50值在纳摩尔范围内，比原来的化合物强很多。抑制机制和动力学特性研究表明它们是不可逆的竞争性抑制剂。