5,10-bis[2-(dimethylamino)ethyl]benzo[de]triazolo[4,5-g]isoquinoline-4,6(5H,10H)-dione | 1353887-20-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,10-bis[2-(dimethylamino)ethyl]benzo[de]triazolo[4,5-g]isoquinoline-4,6(5H,10H)-dione
• 英文别名: 3,11-Bis[2-(dimethylamino)ethyl]-3,11,12,13-tetrazatetracyclo[7.6.1.05,16.010,14]hexadeca-1(15),5,7,9(16),10(14),12-hexaene-2,4-dione
• CAS: 1353887-20-3
• 化学式: C₂₀H₂₄N₆O₂
• 分子量: 380.45
• InChiKey: OXMVKWSROJASQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-amino-naphthalene-1,8-dicarboxylic acid-anhydride 在 nitrosonium tetrafluoroborate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 1.0h， 生成 5,10-bis[2-(dimethylamino)ethyl]benzo[de]triazolo[4,5-g]isoquinoline-4,6(5H,10H)-dione
  参考文献：
  名称：

  Unprecedented synthesis, in vitro and in vivo anti-cancer evaluation of novel triazolonaphthalimide derivatives

  摘要：

  An efficient synthesis method for fusing triazole ring onto the naphthalimide core was described. The anti-cancer activities of the generated triazolonaphthalimide derivatives were evaluated with five cancer cell lines. The compounds generally displayed higher potency than amonafide. 4d,4e carrying two amino side chains showed the strongest cytotoxicities. N-oxide 5, a prodrug of 4a, was designed and synthesized. The agent was expected to be activated under the hypoxic condition in tumor tissue. Compared with 4a, 5 manifested much lower cytotoxicity both in cancer cell lines and human normal cells in the in vitro assays. However, N-oxide 5 performed potent anti-cancer activity in vivo using S-180 sarcoma bearing mice. All the results suggested that 5 was a promising anti-cancer agent. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.11.025

文献信息

• Unprecedented synthesis, in vitro and in vivo anti-cancer evaluation of novel triazolonaphthalimide derivatives
  作者：Shasha Li、Wenhe Zhong、Zhongjun Li、Xiangbao Meng

  DOI：10.1016/j.ejmech.2011.11.025

  日期：2012.1

  An efficient synthesis method for fusing triazole ring onto the naphthalimide core was described. The anti-cancer activities of the generated triazolonaphthalimide derivatives were evaluated with five cancer cell lines. The compounds generally displayed higher potency than amonafide. 4d,4e carrying two amino side chains showed the strongest cytotoxicities. N-oxide 5, a prodrug of 4a, was designed and synthesized. The agent was expected to be activated under the hypoxic condition in tumor tissue. Compared with 4a, 5 manifested much lower cytotoxicity both in cancer cell lines and human normal cells in the in vitro assays. However, N-oxide 5 performed potent anti-cancer activity in vivo using S-180 sarcoma bearing mice. All the results suggested that 5 was a promising anti-cancer agent. (C) 2011 Elsevier Masson SAS. All rights reserved.