3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone | 757996-09-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone
• CAS: 757996-09-1
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: MKEJREONHVVCPE-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone 、 1,2-二氨基-4,5-二甲氧基苯 以 甲醇 为溶剂， 以0.04 g的产率得到1,7,8-trimethoxy-4-[2-(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
• 作为产物：
  描述：

  (Z)-3-甲氧基-6-(3,4,5-三甲氧基苯乙烯)苯-1,2-二醇 在 sodium periodate 、 四丁基溴化铵 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 3-methoxy-6-[2-(3,4,5-trimethoxyphenyl)-Z-ethylene]-[1,2]benzoquinone
  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.