[9-(羟基甲基)萘并[1,2-b]喹啉-7-基]甲醇 | 160543-04-4

• 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: [9-(羟基甲基)萘并[1,2-b]喹啉-7-基]甲醇
• 中文别名: 7,9-二-羟甲基苯并[C]吖啶
• 英文名称: 7,9-bis(hydroxymethyl)benz[c]acridine
• 英文别名: 7,9-Bis(hydroxymethyl)benz(c)acridine；[7-(hydroxymethyl)naphtho[1,2-b]quinolin-9-yl]methanol
• CAS: 160543-04-4
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: TYYRHOGUEROKSQ-UHFFFAOYSA-N

物化性质

• 沸点：
  599.2±30.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  7,9-bis(acetoxymethyl)benz[c]acridine 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 [9-(羟基甲基)萘并[1,2-b]喹啉-7-基]甲醇
  参考文献：
  名称：

  Identification of Hepatic Metabolites of Two Highly Carcinogenic Polycyclic Aza-Aromatic Compounds, 7,9-Dimethylbenz[c]acridine and 7,10-Dimethylbenz[c]acridine

  摘要：

  The hepatic microsomal metabolites of the highly carcinogenic dimethylbenzacridines, 7,9-dimethylbenz[c]acridine (7,9-DMBAC), and 7,10-dimethylbenz[c]acridine (7,10-DMBAC) were obtained with preparations from 3-methylcholanthrene-pretreated rats. Metabolites were separated by reversed-phase HPLC and characterized using UV spectral data and chemical ionization-mass spectrometry after trimethylsilylation and GC. Comparisons with products formed in the presence of the epoxide hydrolase inhibitor, 1,1,1-trichloropropane 2,3-oxide and with those formed from the three synthetic alcohol derivatives of each parent compound, aided the assignment of firm or tentative structures to 16 products from 7,9-DMBAC found in 22 reversed-phase chromatographic peaks, and for 17 products of 7,10-DMBAC found in 19 chromatographic peaks. The more abundant metabolites were derived from oxidation of the methyl groups. Other metabolites were dihydrodiols, epoxides, phenols and secondary metabolites. The 9-methyl group prevented dihydrodiol formation at the 8,9-position from 7,9-DMBAC, and for each carcinogen, the 3,4-dihydrodiol was formed. As well, 3,4-dihydrodiols of methyl oxidized compounds were found.

  DOI：

  10.1021/tx00044a003

文献信息

• Identification of Hepatic Metabolites of Two Highly Carcinogenic Polycyclic Aza-Aromatic Compounds, 7,9-Dimethylbenz[c]acridine and 7,10-Dimethylbenz[c]acridine
  作者：Yuerong Ye、Colin C. Duke、Gerald M. Holder

  DOI：10.1021/tx00044a003

  日期：1995.3

  The hepatic microsomal metabolites of the highly carcinogenic dimethylbenzacridines, 7,9-dimethylbenz[c]acridine (7,9-DMBAC), and 7,10-dimethylbenz[c]acridine (7,10-DMBAC) were obtained with preparations from 3-methylcholanthrene-pretreated rats. Metabolites were separated by reversed-phase HPLC and characterized using UV spectral data and chemical ionization-mass spectrometry after trimethylsilylation and GC. Comparisons with products formed in the presence of the epoxide hydrolase inhibitor, 1,1,1-trichloropropane 2,3-oxide and with those formed from the three synthetic alcohol derivatives of each parent compound, aided the assignment of firm or tentative structures to 16 products from 7,9-DMBAC found in 22 reversed-phase chromatographic peaks, and for 17 products of 7,10-DMBAC found in 19 chromatographic peaks. The more abundant metabolites were derived from oxidation of the methyl groups. Other metabolites were dihydrodiols, epoxides, phenols and secondary metabolites. The 9-methyl group prevented dihydrodiol formation at the 8,9-position from 7,9-DMBAC, and for each carcinogen, the 3,4-dihydrodiol was formed. As well, 3,4-dihydrodiols of methyl oxidized compounds were found.