7-chloro-2-thien-2-ylcarbonyl-3-trifluoromethylquinoxaline 4-oxide | 1233700-49-6

• 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: 7-chloro-2-thien-2-ylcarbonyl-3-trifluoromethylquinoxaline 4-oxide
• 英文别名: 7-Chloro-2-(thien-2-ylcarbonyl)3-trifluoromethylquinoxaline-4-oxide；[7-chloro-4-oxido-3-(trifluoromethyl)quinoxalin-4-ium-2-yl]-thiophen-2-ylmethanone
• CAS: 1233700-49-6
• 化学式: C₁₄H₆ClF₃N₂O₂S
• 分子量: 358.728
• InChiKey: DWVYQZGSKPJCIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  83.7
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-chloro-2-thien-2-ylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide 在 cytochrome P₄₅₀ reductase 、 去铁胺 、 还原型辅酶II(NADPH)四钠盐 、 superoxide dismutase 、 catalase 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 7-chloro-2-thien-2-ylcarbonyl-3-trifluoromethylquinoxaline 1-oxide 、 7-chloro-2-thien-2-ylcarbonyl-3-trifluoromethylquinoxaline 4-oxide
  参考文献：
  名称：

  DNA strand cleaving properties and hypoxia-selective cytotoxicity of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide

  摘要：

  The heterocyclic N-oxide, 3-amino-1,2,4-benzotriazine 1,4-dioxide (tirapazamine, 1), shows promising antitumor activity in preclinical studies, but there is a continuing need to explore new compounds in this general structural category. In the work described here, we examined the properties of 7-chloro-2-thienylcarbonyl-3-trifluoromethylquinoxaline 1,4-dioxide (9h). We find that 9h causes redox-activated, hypoxia-selective DNA cleavage that mirrors the lead compound, tirapazamine, in both mechanism and potency. Furthermore, we find that 9h displays hypoxia-selective cytotoxicity against human cancer cell lines. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.042