N-(glutathion-S-yl)-1,4-benzoquinonimine | 220153-14-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(glutathion-S-yl)-1,4-benzoquinonimine
• 英文别名: (2S)-2-amino-5-[[(2R)-1-(carboxymethylamino)-1-oxo-3-[(4-oxocyclohexa-2,5-dien-1-ylidene)amino]sulfanylpropan-2-yl]amino]-5-oxopentanoic acid
• CAS: 220153-14-0
• 化学式: C₁₆H₂₀N₄O₇S
• 分子量: 412.423
• InChiKey: LCIAVRXLCZOOCE-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  214
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N-(glutathion-S-yl)-1,4-benzoquinonimine 在 Cleland's reagent 作用下， 以 重水 为溶剂， 生成 N-(glutathion-S-yl)-4-aminophenol
  参考文献：
  名称：

  Additional Pathways of S-Conjugate Formation during Interaction of 4-Nitrosophenetole with Glutathione

  摘要：

  The rapid reactions of nitrosoarenes with cellular SH groups have proved to be main metabolic conversions during detoxication. Inter actions of the phenacetin metabolite 4-nitrosophenetole with glutathione have been investigated in detail during the last years, revealing a complete pattern of products depending on the stoichiometry of the reactants and reaction conditions Eight metabolites have been identified hitherto, and the present work extends this medley by six additional products. Three metastable sulfenamides, 4-ethoxy-2,N-bis(glutathion-S-yl)-aniline, N-4-glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine, and N-(glutathion-S-yl)-4-aminophenol, as well as the N-sulfenylquinonimine N-(glutathion-S-yl)-1,4-benzoquinonimine were characterized by chemical reactivity, chromatographic behavior, UV/vis absorption, H-1 NMR, and FAB-MS data. The structure of the sulfenamide 2,N-4-bis(glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine could not be proved unequivocally, but is strongly suggested due to the chemical reactivity? chromatographic behavior, and UV/vis absorption of the compound. Finally, traces of 4-aminophenol were detected. A reaction scheme is presented explaining the formation of all identified metabolites via a central sulfenamide cation. Molecular orbital calculations for this sulfenamide cation have been performed, corroborating the proposed reaction mechanisms on the basis of Klopman's generalized perturbation theory.

  DOI：

  10.1021/tx980087q
• 作为产物：
  描述：

  1-乙氧基-4-亚硝基苯 以 甲醇 、 phosphate buffer 为溶剂， 反应 72.0h， 生成 N-(glutathion-S-yl)-1,4-benzoquinonimine
  参考文献：
  名称：

  Additional Pathways of S-Conjugate Formation during Interaction of 4-Nitrosophenetole with Glutathione

  摘要：

  The rapid reactions of nitrosoarenes with cellular SH groups have proved to be main metabolic conversions during detoxication. Inter actions of the phenacetin metabolite 4-nitrosophenetole with glutathione have been investigated in detail during the last years, revealing a complete pattern of products depending on the stoichiometry of the reactants and reaction conditions Eight metabolites have been identified hitherto, and the present work extends this medley by six additional products. Three metastable sulfenamides, 4-ethoxy-2,N-bis(glutathion-S-yl)-aniline, N-4-glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine, and N-(glutathion-S-yl)-4-aminophenol, as well as the N-sulfenylquinonimine N-(glutathion-S-yl)-1,4-benzoquinonimine were characterized by chemical reactivity, chromatographic behavior, UV/vis absorption, H-1 NMR, and FAB-MS data. The structure of the sulfenamide 2,N-4-bis(glutathion-S-yl)-4-amino-4'-ethoxydiphenylamine could not be proved unequivocally, but is strongly suggested due to the chemical reactivity? chromatographic behavior, and UV/vis absorption of the compound. Finally, traces of 4-aminophenol were detected. A reaction scheme is presented explaining the formation of all identified metabolites via a central sulfenamide cation. Molecular orbital calculations for this sulfenamide cation have been performed, corroborating the proposed reaction mechanisms on the basis of Klopman's generalized perturbation theory.

  DOI：

  10.1021/tx980087q