5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-yl phosphoric acid dimethyl ester | 1453477-46-7

• 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 dimethyl ester
• 英文别名: 5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl dimethylphosphate；5-Hydroxy-4-oxo-2-phenyl-4h-chromen-7-yl di-methyl phosphate；(5-hydroxy-4-oxo-2-phenylchromen-7-yl) dimethyl phosphate
• CAS: 1453477-46-7
• 化学式: C₁₇H₁₅O₇P
• 分子量: 362.276
• InChiKey: LOXUMMFHARHYIJ-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  510.4±50.0 °C(predicted)
• 密度：
  1.420±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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 、 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58%的产率得到5-hydroxy-4-oxo-2-phenyl-4H-1-benzopyran-7-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

文献信息

• 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。