1-methoxy-4-[(3,4,5-trimethoxyphenyl)-Z-vinyl]phenazine | 1061756-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-methoxy-4-[(3,4,5-trimethoxyphenyl)-Z-vinyl]phenazine
• 英文别名: 1-methoxy-4-[(Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenazine
• CAS: 1061756-87-3
• 化学式: C₂₄H₂₂N₂O₄
• 分子量: 402.45
• InChiKey: BBEYYVHZKGKNNM-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone 、 邻苯二胺 以 甲醇 为溶剂， 以30 mg的产率得到1-methoxy-4-[(3,4,5-trimethoxyphenyl)-Z-vinyl]phenazine
  参考文献：
  名称：

  Antineoplastic Agents. 552. Oxidation of Combretastatin A-1: Trapping the o-Quinone Intermediate Considered the Metabolic Product of the Corresponding Phosphate Prodrug

  摘要：

  The very unstable (<10 min at rt) o-quinone 5 derived from the vicinal diphenol anticancer drug combretastatin A-1 (1) has been obtained by careful oxidation with NaIO4 and tetrabutylammonium bromide in water/dichloromethane. Immediate reaction with phenylenediamine (6) allowed o-quinone 5 to be trapped as the stable phenazine derivative 7. For further confirmation, 5 was also captured as a dimethoxyphenylenediamine-derived phenazine (11). Both phenazines 7 and 11 significantly inhibited (ED50 similar to 0.2 mu g/mL) growth of the murine P388 lymphocytic leukemia cell line and provided a new SAR insight in the combretastatin series of naturally occurring anticancer drugs.

  DOI：

  10.1021/np800179g

文献信息

• Antineoplastic Agents. 552. Oxidation of Combretastatin A-1: Trapping the <i>o</i>-Quinone Intermediate Considered the Metabolic Product of the Corresponding Phosphate Prodrug
  作者：George R. Pettit、Andrew J. Thornhill、Bryan R. Moser、Fiona Hogan

  DOI：10.1021/np800179g

  日期：2008.9.1

  The very unstable (<10 min at rt) o-quinone 5 derived from the vicinal diphenol anticancer drug combretastatin A-1 (1) has been obtained by careful oxidation with NaIO4 and tetrabutylammonium bromide in water/dichloromethane. Immediate reaction with phenylenediamine (6) allowed o-quinone 5 to be trapped as the stable phenazine derivative 7. For further confirmation, 5 was also captured as a dimethoxyphenylenediamine-derived phenazine (11). Both phenazines 7 and 11 significantly inhibited (ED50 similar to 0.2 mu g/mL) growth of the murine P388 lymphocytic leukemia cell line and provided a new SAR insight in the combretastatin series of naturally occurring anticancer drugs.