N-((phenoxy)((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-alanine methyl 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: N-((phenoxy)((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-alanine methyl ester
• 英文别名: methyl (2S)-2-[[[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxochromen-7-yl]oxy-phenoxyphosphoryl]amino]propanoate
• 化学式: C₂₉H₂₆NO₁₁P
• 分子量: 595.499
• InChiKey: ZZRFABNDQVNGPI-DXTJSGOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-((phenoxy)((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-alanine methyl ester 在 四氢吡咯 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到N-((phenoxy)((5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-alanine 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
• 作为产物：
  描述：

  德国春黄菊油 在 吡啶 、 咪唑 、 potassium carbonate 、 苯硫酚 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 丙酮 为溶剂， 反应 5.0h， 生成 N-((phenoxy)((5-acetoxy-2-(4-acetoxyphenyl)-4-oxo-4H-chromene-7-yl)oxy)phosphoryl)-L-alanine 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

• 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.