N-((phenoxy)((5-hydroxy-2-phenyl-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)glycine methyl ester | 1191941-59-9

• 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: N-((phenoxy)((5-hydroxy-2-phenyl-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)glycine methyl ester
• 英文别名: Methyl 2-[[(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxy-phenoxyphosphoryl]amino]acetate；methyl 2-[[(5-hydroxy-4-oxo-2-phenylchromen-7-yl)oxy-phenoxyphosphoryl]amino]acetate
• CAS: 1191941-59-9
• 化学式: C₂₄H₂₀NO₈P
• 分子量: 481.398
• InChiKey: SMLBUUJNHKMMIR-UHFFFAOYSA-N

物化性质

• 熔点：
  156-157 °C
• 沸点：
  653.1±65.0 °C(Predicted)
• 密度：
  1.417±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  二氯磷酸苯酯 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 N-((phenoxy)((5-hydroxy-2-phenyl-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)glycine methyl ester
  参考文献：
  名称：

  Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines

  摘要：

  A series of flavone-7-phosphoramidate derivatives were synthesized and tested for their antiproliferative activity in vitro against human hepatoma cell line HepG2 and human normal hepatic cell line L-O2. Compound 8d, 16d and 17d, incorporating the amino acid alanine, exhibited high inhibitory activity on HepG2 cell line with IC50 values of 9.0 mu mol/L, 5.5 mu mol/L and 6.6 mu mol/L. The introduction of acyl groups played a pivotal role in the selective inhibition toward human hepatoma HepG2 cells, except for compound 8a, 9a and 16b. Compound 8d, 16d and 17d could significantly induce G2/M arrest in HepG2 cells. Specially, Compound 16d could lead early apoptosis in HepG2 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.02.012

文献信息

• Synthesis of the Novel Phosphoramidate Derivatives of Chrysin
  作者：Xiaolan Chen、Jinwei Yuan、Shouren Zhang、Lingbo Qu、Yufen Zhao

  DOI：10.1080/10426500902772858

  日期：2010.1.29

  A novel type of phosphoramidate derivatives of chrysin were synthesized by a facile phosphorylation reaction. The structures of all the newly synthesized chrysin derivatives were confirmed by ESI MS, HR MS, NMR, and IR.
• Phosphoramidate protides of five flavones and their antiproliferative activity against HepG2 and L-O2 cell lines
  作者：Yue-qing Li、Fei Yang、Liu Wang、Zhi Cao、Tian-jiao Han、Zhe-ang Duan、Zhen Li、Wei-jie Zhao

  DOI：10.1016/j.ejmech.2016.02.012

  日期：2016.4

  A series of flavone-7-phosphoramidate derivatives were synthesized and tested for their antiproliferative activity in vitro against human hepatoma cell line HepG2 and human normal hepatic cell line L-O2. Compound 8d, 16d and 17d, incorporating the amino acid alanine, exhibited high inhibitory activity on HepG2 cell line with IC50 values of 9.0 mu mol/L, 5.5 mu mol/L and 6.6 mu mol/L. The introduction of acyl groups played a pivotal role in the selective inhibition toward human hepatoma HepG2 cells, except for compound 8a, 9a and 16b. Compound 8d, 16d and 17d could significantly induce G2/M arrest in HepG2 cells. Specially, Compound 16d could lead early apoptosis in HepG2 cells. (C) 2016 Elsevier Masson SAS. All rights reserved.