nitracrine N-oxide | 20064-09-9

• 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
• 英文名称: nitracrine N-oxide
• 英文别名: Nitracrine-N(10)-oxide；N',N'-dimethyl-N-(1-nitro-10-oxidoacridin-10-ium-9-yl)propane-1,3-diamine
• CAS: 20064-09-9
• 化学式: C₁₈H₂₀N₄O₃
• 分子量: 340.382
• InChiKey: ZSAPXVXHFFLXCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  85.35
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 nitracrine N-oxide 在 rat liver cytosol 作用下， 以 phosphate buffer 为溶剂， 反应 2.5h， 生成 1-(S-Glutathionyl)-9-(3'-dimethylamino-N-propylamino)-acridine-N(10)-oxide
  参考文献：
  名称：

  Effect of substituents on the metabolism of nitracrine in rat

  摘要：

  1. Male Wistar rats were treated with either the antitumour agent nitracrine (1-nitro-9-(3'-dimethylamino-N-propylamino)-acridine ; NC), 4-methoxy-NC, NC-aliphatic-N-oxide, 4-methoxy-NC-aliphatic-N-oxide, or NC-aromatic N-oxide (30 mu mol/kg, via the femoral vein) and the major biliary and urinary metabolites analysed by hplc.2. No NC or 4-methoxy-NC were detected in bile or urine of rat treated with NC or 4-methoxy-NC respectively, whereas the aliphatic N-oxides of NC and 4-methoxy-NC were recovered largely unchanged in both bile and urine.3. NC-aromatic-N-oxide was rapidly and extensively converted to a major polar biliary product. This product was also synthesised enzymatically from NC-aromatic-N-oxide using rat liver cytosol and has been identified by mass and H-1-nmr spectrometry as 1-(S-gluthathionyl)-9-(3'-dimethylamino-N-propylamino)-acridine-N(10)-oxide.4. The equivalent 1-(S-glutathionyl) conjugate appears to be formed from NC, and excreted in bile as a minor product, but not from 4-methoxy-NC. Further experiments with cytosol indicate that direct displacement of the nitro group by GSH is mediated by GSH transferase.5. Finally, the major biliary metabolite of NC has been provisionally identified as a glucuronide of 1-nitro-2-hydroxy-NC.6. It is concluded that, for at least a significant fraction of NC, nitroreduction does not occur. Further, N-oxidation of the aliphatic (but not the aromatic ring) nitrogen, plus 4-methoxy substitution, decreases the overall metabolism of NC in the rat.

  DOI：

  10.3109/00498259609046732