二乙基黄酮-7-基磷酸酯 | 102080-28-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 二乙基黄酮-7-基磷酸酯
• 英文名称: diethyl flavon-7-yl phosphate
• 英文别名: 7-diethoxyphosphoryloxy-2-phenyl-chromen-4-one；7-Diaethoxyphosphoryloxy-2-phenyl-chromen-4-on；Diethyl (4-oxo-2-phenylchromen-7-yl) phosphate
• CAS: 102080-28-4
• 化学式: C₁₉H₁₉O₆P
• 分子量: 374.33
• InChiKey: RPLAJNAANULVOX-UHFFFAOYSA-N

物化性质

• 熔点：
  60-61 °C
• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

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：

  特普 、 7-羟基黄酮 在 sodium hydroxide 作用下， 生成 二乙基黄酮-7-基磷酸酯
  参考文献：
  名称：

  6：8-二羟基黄酮的合成

  摘要：

  描述了合成6：8-二羟基黄酮的途径的工作，其中一种被证明是成功的。

  DOI：

  10.1016/0040-4020(58)88029-1

文献信息

• 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。
• Synthesis of Novel Phosphoric Esters of Flavone and Isoflavone by Atherton–Todd Reaction
  作者：Xiaolan Chen、Youzhu Yu、Lingbo Qu、Xincheng Liao、Yufen Zhao

  DOI：10.1081/scc-120027289

  日期：2004.12.31

  Abstract 7‐hydroxyflavone, chrysin, 4′‐chloro‐7‐hydroxyisoflavone and 4′‐fluo‐7‐hydroxy‐isoflavone were phosphoylated by the Atheron–Todd reaction. The expected phosphates are obtained in good yields.

  摘要 7-羟基黄酮、白杨素、4'-氯-7-羟基异黄酮和4'-氟-7-羟基-异黄酮通过Atheron-Todd反应被磷酸化。以良好的产率获得了预期的磷酸盐。
• Flavonoid Compounds and Uses Thereof
  申请人：Jarrott Bevyn

  公开号：US20090130051A1

  公开（公告）日：2009-05-21

  Novel flavonoid compounds having anti-oxidant activity are described. The compounds and compositions have been shown to exhibit anti-oxidant properties and are particularly useful in the treatment of ischemia and reperfusion injuries. The invention also describes a method to chemically synthesize such flavonoid compounds and test their efficacy. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have uses in the areas of pharmaceuticals, nutraceutical, and veterinary applications.

  本发明描述了具有抗氧化活性的新型黄酮类化合物。这些化合物和组合物已被证明具有抗氧化性质，特别适用于缺血和再灌注损伤的治疗。本发明还描述了一种化学合成这种黄酮类化合物并测试其功效的方法。这些化合物及其对应的药学上可接受的衍生物和/或盐在制药、保健品和兽医应用领域中有用。
• 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 synthesis of 6:8-dihydroxyflavone
  作者：J.E. Gown、S.P.MacGiolla Riogh、G.J. MacMahon、S. Ó'Cléirigh、E.M. Philbin、T.S. Wheeler

  DOI：10.1016/0040-4020(58)88029-1

  日期：1958.1

  Work on routes to the synthesis of 6:8-dihydroxyflavone, one of which proved successful, is described.

  描述了合成6：8-二羟基黄酮的途径的工作，其中一种被证明是成功的。