2-(2-Methylpropyl)triazolo[4,5-g]phthalazine-4,9-dione | 1029797-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-Methylpropyl)triazolo[4,5-g]phthalazine-4,9-dione
• CAS: 1029797-86-1
• 化学式: C₁₂H₁₁N₅O₂
• 分子量: 257.252
• InChiKey: PCUUECDOHPWNCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1H-[1,2,3]triazolo[4,5-g]phthalazine-4,9-dione 、 碘代异丁烷 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以13 mg的产率得到2-(2-Methylpropyl)triazolo[4,5-g]phthalazine-4,9-dione
  参考文献：
  名称：

  Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine-4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition

  摘要：

  Studies on antitumor heterocyclic quinones containing nitrogens revealed that the number and position of nitrogens on the heterocyclic ring have significance on cytotoxicity of quinones. In our continuous effort to find more cytotoxic quinone compounds, we designed triazolophthalazine analogues in order to introduce more nitrogens on the heterocyclic quinones. 1-/2-Substituted[ 1,2,3]triazolo[4,5-g] phthalazine-4,9-diones were synthesized by 1,3-dipolar addition of phthalazine-5,8-dione and 4-methoxybenzyl azide by modi. cation of previously reported method. The cytotoxicity of the synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against nine types of human cancer cell lines and inhibition against topoisomerase II (Topo II) of them was assessed by a decatenation assay. Most of the synthesized compounds showed considerably higher cytotoxicity than that of doxorubicin. Also, topoisomerase II inhibitory activity of the tested compounds was higher than that of etoposide and IC50 values of the compounds were 19.4-64.5 mu M. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.02.049

文献信息

• Synthesis of 1-/2-substituted-[1,2,3]triazolo[4,5-g]phthalazine-4,9-diones and evaluation of their cytotoxicity and topoisomerase II inhibition
  作者：Jin Sung Kim、Hee-Kyung Rhee、Hyen Joo Park、Sang Kook Lee、Chong-Ock Lee、Hea-Young Park Choo

  DOI：10.1016/j.bmc.2008.02.049

  日期：2008.4

  Studies on antitumor heterocyclic quinones containing nitrogens revealed that the number and position of nitrogens on the heterocyclic ring have significance on cytotoxicity of quinones. In our continuous effort to find more cytotoxic quinone compounds, we designed triazolophthalazine analogues in order to introduce more nitrogens on the heterocyclic quinones. 1-/2-Substituted[ 1,2,3]triazolo[4,5-g] phthalazine-4,9-diones were synthesized by 1,3-dipolar addition of phthalazine-5,8-dione and 4-methoxybenzyl azide by modi. cation of previously reported method. The cytotoxicity of the synthesized compounds was evaluated by a SRB (sulforhodamine B) assay against nine types of human cancer cell lines and inhibition against topoisomerase II (Topo II) of them was assessed by a decatenation assay. Most of the synthesized compounds showed considerably higher cytotoxicity than that of doxorubicin. Also, topoisomerase II inhibitory activity of the tested compounds was higher than that of etoposide and IC50 values of the compounds were 19.4-64.5 mu M. (c) 2008 Elsevier Ltd. All rights reserved.