2-Hydroxy-3,4-benzo-phenazin-5,10-dioxid | 26390-71-6

• 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: 2-Hydroxy-3,4-benzo-phenazin-5,10-dioxid
• 英文别名: 5-Hydroxybenzophenazin-7,12-dioxid；5-hydroxybenzo[a]phenazine 7,12-dioxide；7,12-dioxy-benzo[a]phenazin-5-ol；5-Hydroxybenzo[a]phenazine 7,12-dioxide；7,12-dioxidobenzo[a]phenazine-7,12-diium-5-ol
• CAS: 26390-71-6
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: TZJYERXUQHSITJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯并呋咱 、 萘酚 在 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以35%的产率得到2-Hydroxy-3,4-benzo-phenazin-5,10-dioxid
  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

文献信息

• A new route for the synthesis of phenazine di-N-oxides
  作者：M. S. Abd El-Halim、A. S. El-Ahl、H. A. Etman、M. M. Ali、A. Fouda、A. A. Fadda

  DOI：10.1007/bf00824300

  日期：1995.11
• Study of benzo[a]phenazine 7,12-dioxide as selective hypoxic cytotoxin-scaffold. Identification of aerobic-antitumoral activity through DNA fragmentation
  作者：María Laura Lavaggi、Mauricio Cabrera、María de los Ángeles Aravena、Claudio Olea-Azar、Adela López de Ceráin、Antonio Monge、Gisela Pachón、Marta Cascante、Ana María Bruno、Lía I. Pietrasanta

  DOI：10.1016/j.bmc.2010.04.074

  日期：2010.6.15

  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.