8-benzyloxy-2,3-dimethoxybenzo[i]phenanthridine | 618437-13-1

• 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: 8-benzyloxy-2,3-dimethoxybenzo[i]phenanthridine
• 英文别名: 2,3-Dimethoxy-8-phenylmethoxybenzo[i]phenanthridine
• CAS: 618437-13-1
• 化学式: C₂₆H₂₁NO₃
• 分子量: 395.458
• InChiKey: RZQWWIFLBKFRMB-UHFFFAOYSA-N

物化性质

• 熔点：
  227-228 °C
• 沸点：
  610.1±50.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-benzyloxy-2,3-dimethoxybenzo[i]phenanthridine 在 镍 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 反应 45.0h， 以86%的产率得到2,3-Dimethoxy-benzo[i]phenanthridin-8-ol
  参考文献：
  名称：

  2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents

  摘要：

  Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase 1-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase 1-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase 1-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase 1-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3 substituents at the 8-position on the relative activity of these 2,3 -dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00530-8
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢-1H-2-萘酮 在 四(三苯基膦)钯 三溴化磷 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 copper(I) bromide 、 锌 作用下， 以 四氢呋喃 、 氯仿 、 甲苯 为溶剂， 反应 29.0h， 生成 8-benzyloxy-2,3-dimethoxybenzo[i]phenanthridine
  参考文献：
  名称：

  2,3-Dimethoxybenzo[i]phenanthridines: topoisomerase I-targeting anticancer agents

  摘要：

  Appropriately substituted benzo[i]phenanthridines structurally related to nitidine, a benzo[c]phenanthridine alkaloid with antitumor activity, are active as topoisomerase 1-targeting agents. Studies on benzo[i]phenanthridines have indicated analogues that possess a 2,3-methylenedioxy moiety and at least one and preferably two methoxyl groups at the 8- and 9-positions, such as 8,9-dimethoxy-2,3-methylenedioxybenzo[i]phenanthridine, 2, are active as topoisomerase 1-targeting agents. Tetramethoxylated benzo[i]phenanthridines, wherein the 2,3-methylenedioxy moiety is replaced with methoxyl groups at the 2- and 3-position, are inactive as a topoisomerase 1-targeting agent. These results initially suggested that the 2,3-methylenedioxy moiety was critical to the retention of potent activity. Further studies revealed that 2,3-dimethoxy-8,9-methylenedioxybenzo[i]phenanthridine, 7a, is more potent than 2 as a topoisomerase 1-targeting agent. The observation that 2,3-dimethoxylated benzo[i]phenanthridines can actually exhibit enhanced activity prompted the present study in which several 8-substituted 2,3-dimethoxybenzo[i]phenanthridines were prepared and their pharmacological activities evaluated. The influence of NH2, CN, CH2OH, OBn, OCH3, OH, and NHCOCH3 substituents at the 8-position on the relative activity of these 2,3 -dimethoxybenzo[i]phenanthridines was examined. Relative to these derivatives, 7a was the most potent topoisomerase I-targeting agent, possessing similar cytotoxicity to that of nitidine in the human lymphoblast tumor cell line, RPMI8402. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00530-8