5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid diethyl ester

• 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: 5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid diethyl ester
• 英文别名: 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl diethylphosphate；5-Hydroxy-4-oxo-2-phenyl-4h-chromen-7-yl di-ethyl phosphate；diethyl (5-hydroxy-4-oxo-2-phenylchromen-7-yl) phosphate
• 化学式: C₁₉H₁₉O₇P
• 分子量: 390.329
• InChiKey: VCEBKFUGAHWSFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 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：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白杨素 、 氯磷酸二乙酯 在 吡啶 作用下， 反应 24.0h， 以69%的产率得到5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid diethyl ester
  参考文献：
  名称：

  磷酸化白杨素衍生物的合成及其对羧酸酯酶的抑制活性的效率和选择性的估计

  摘要：

  寻找新的选择性和有效的羧酸酯酶抑制剂是一个相当热门的问题[1-4]。丝氨酸酯酶亚类的酶包括乙酰胆碱酯酶、丁酰胆碱酯酶、胆固醇酯酶等，在羧酸酯酶之上具有相似的活性中心结构[5, 6]。因此，单一化合物可以潜在地抑制该亚类的所有酶。因此，丝氨酸酯酶抑制剂的研究应始终考虑选择性问题。使用丝氨酸酯酶的选择性抑制剂应该允许优先调节酯化异生物质（包括药物）的代谢。

  DOI：

  10.1134/s1070363216020419

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.
• Chrysin and its phosphate ester inhibit cell proliferation and induce apoptosis in Hela cells
  作者：Ting Zhang、Xiaolan Chen、Lingbo Qu、Jinglan Wu、Ran Cui、Yufen Zhao

  DOI：10.1016/j.bmc.2004.09.013

  日期：2004.12

  To improve the biological activities of chrysin (CR), we synthesize Diethyl Chysin-7-yl phosphate (CPE: C19H19O7P) and tetraethyl bis-phosphoric ester of chrysin (CP: C23H28O10P2) through a simplified Atheron Todd reaction. The interactions of the CR and CPE with lysozyme were explored by electrospray ionization mass spectrometry (ESI) and fluorescence spectrometry method. Experimental results indicate that CPE could form the noncovalent compound with lysozyme, while the interaction of the CR with lysozyme was not detected. In addition, whether and how the compounds CPE and CP affect proliferation and apoptosis in human cervical cancer Hela cells were investigated. Moreover, the effects of CPE and CP in Hela cells were compared with that of the nonmodified CR compound. The Hela cells were co-cultured with CR, CP, and CPE as experimental groups, respectively, and corresponding control groups treated without CR, CP, and CPE. The proliferation and apoptosis were detected using MTT assay, HCl denatured-methyl green-pyronin staining, PCNA immunohistochemistry and TUNEL techniques. The cell growth IC50, relative absorbance (RA), proliferating index (PI), PCNA-IR (immunoreactivity IR) integration value (IV), and apoptosis index (AI) were calculated and their correlation was analyzed in each group. The results show that all CR, CP, and CPE could inhibit proliferation and induce apoptosis in Hela cells. Moreover, the effects of CP and CPE were more potent than that of CR. The CP and CPE were proved to be a kind of stronger apoptosis inducers than nonphosphated CR. There was a negative correlation between proliferation and apoptosis. In conclusion, the CR, CP, and CPE could effectively inhibit growth by down-regulated expression of PCNA, and induce apoptosis in Hela cells. The efficiency of the modified CP and CPE preceded nonmodified CR compounds. The CP and CPE may be a new potential anti-cancer drug for therapy of human cervical carcinoma. (C) 2004 Published by Elsevier Ltd.
• Synthesis of phosphorylated chrysin derivatives and estimation of efficiency and selectivity of their inhibitory activity towards carboxylesterase
  作者：V. V. Abzianidze、D. S. Prokofieva、A. S. Bogachenkov

  DOI：10.1134/s1070363216020419

  日期：2016.2

  for the new selective and efficient inhibitors of carboxylesterases is a fairly topical issue [1–4]. The enzymes of serine esterase subclass including acetylcholinesterase, butyrylcholinesterase, cholesterol esterase, and others on top of carboxylesterase have a similar structure of the active center [5, 6]. Consequently, a single compound can potentially inhibit all the enzymes of this subclass. Therefore

  寻找新的选择性和有效的羧酸酯酶抑制剂是一个相当热门的问题[1-4]。丝氨酸酯酶亚类的酶包括乙酰胆碱酯酶、丁酰胆碱酯酶、胆固醇酯酶等，在羧酸酯酶之上具有相似的活性中心结构[5, 6]。因此，单一化合物可以潜在地抑制该亚类的所有酶。因此，丝氨酸酯酶抑制剂的研究应始终考虑选择性问题。使用丝氨酸酯酶的选择性抑制剂应该允许优先调节酯化异生物质（包括药物）的代谢。