5-hydroxy-9-methylbenzo[a]phenazine 7,12-dioxide | 1239664-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-hydroxy-9-methylbenzo[a]phenazine 7,12-dioxide
• CAS: 1239664-76-6
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: HURRQHSDOPNENF-UHFFFAOYSA-N

物化性质

• 沸点：
  611.4±65.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.11
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-甲基苯并呋喃-1-氧化物 、 萘酚 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 5-hydroxy-9-methylbenzo[a]phenazine 7,12-dioxide 、 5-hydroxy-10-methylbenzo[a]phenazine 7,12-dioxide
  参考文献：
  名称：

  Study of benzo[a]phenazine 7,12-dioxide as selective hypoxic cytotoxin-scaffold. Identification of aerobic-antitumoral activity through DNA fragmentation

  摘要：

  Phenazine 5,10-dioxides are prodrugs for antitumor therapy that undergo hypoxic-selective bioreduction to form cytotoxic species. Here we investigate the expanded system benzo[a]phenazine 7,12-dioxides as selective hypoxic cytotoxin-scaffold. The clonogenic survival of V79 cells on aerobic and anaerobic conditions, conduct us to study antiproliferative activity on Caco-2 tumoral cells in normoxia. Electrochemical, DNA-interaction and DNA-damage studies were performed to establish the mode of action. The results demonstrated the potential biological properties of the studied scaffold being derivatives 6-10 structural hits for further chemical-modifications to become into therapeutics for solid tumors. Compounds 6 and 8 with cytotoxicity against V79 cells in both conditions (aerobia and anaerobia) were also cytotoxic against Caco-2 tumoral cells in aerobiosis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.074