3-甲基-2-硝基-3H-咪唑并[4,5-F]喹啉-2-14C | 161406-39-9

• 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
• 中文名称: 3-甲基-2-硝基-3H-咪唑并[4,5-F]喹啉-2-14C
• 英文名称: <2-(14)C>-3-methyl-2-nitro-imidazo<4,5-f>quinoline
• 英文别名: 3-Methyl-2-nitro-3H-imidazo[4,5-F]quinoline-2-14C；3-methyl-2-nitro(214C)imidazolo[4,5-f]quinoline
• CAS: 161406-39-9
• 化学式: C₁₁H₈N₄O₂
• 分子量: 230.199
• InChiKey: JQICQDTZNZTBEZ-OZUIXNLOSA-N

物化性质

• 熔点：
  277-278°C
• 溶解度：
  可溶于二甲基甲酰胺（热）、二甲基亚砜、甲醇（热）

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  76.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [14C]-IQ 在 硫酸 、 copper(II) sulfate 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 24.0h， 以8.67%的产率得到<2-(14)C>-3-methyl-2-nitroso-imidazo<4,5-f>quinoline
  参考文献：
  名称：

  Prostaglandin-H synthase mediated metabolism and mutagenic activation of 2-amino-3-methylimidazo [4,5-f] quinoline (IQ)

  摘要：

  Prostaglandin-H synthase (PHS), a mammalian peroxidase of interest for the extrahepatic formation of reactive intermediates of carcinogens, catalyzes in vitro the metabolic activation of the mutagen and carcinogen 2-amino-3-methylimidazo[4,5-f]quinoline (IQ). Incubation of C-14-labeled IQ with ram seminal vesicle microsomes (RSVM), a rich source of PHS, resulted in protein binding and generated products mutagenic in S. typhimurium YG1024. The mutagenic activity produced in IQ/PHS incubations was stable and extractable with ethyl acetate. Upon fractionation of such extracts by HPLC and subsequent analysis, two metabolites were identified as 2,2'-azo-bis-3-methylimidazo[4,5-f]quinoline (azo-IQ) and 3-methyl-2-nitro-imidazo[4,5-f]quinoline (nitro-IQ) confirmed by comparison of HPLC retention times, UV/VIS-, H-1-NMR-spectroscopy, and mass spectrometry of synthesized standards. Azo-IQ was obtained by chemical oxidation of IQ with metasodium periodate. It was the major metabolite in PHS incubations, but has not been detected in monooxygenase incubations. Azo-IQ, without metabolic activation, was much less mutagenic in S. typhimurium YG1024 (308 rev/nmol) than nitro-IQ and 3-methyl-2-nitroso-imidazo[4,5-f]quinoline (nitroso-IQ), two other S9-independent mutagens which have been synthesized by chemical oxidation of IQ with sodium nitrite. Nitro-IQ was formed only in trace amounts but due to its potent mutagenicity in S. typhimurium YG1024 (2 x 10(6) rev/nmol) it accounted for most of the mutagenic activity of the incubations. These data show that PHS-mediated in vitro metabolism of IQ results in its metabolic activation; thus PHS may contribute to the genotoxicity of IQ in extrahepatic tissues.

  DOI：

  10.1007/s002040050154