4'-nitrophenyl (1-methyl-2-phenylethyl)carbamate | 31364-77-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4'-nitrophenyl (1-methyl-2-phenylethyl)carbamate
• CAS: 31364-77-9；33534-17-7
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: BWEIARVNGBVRBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  L-半胱氨酸 、 4'-nitrophenyl (1-methyl-2-phenylethyl)carbamate 以 水 、 乙腈 为溶剂， 反应 1.5h， 以19%的产率得到S-((1-methyl-2-phenylethyl)carbamoyl)-L-cysteine
  参考文献：
  名称：

  Characterization of Novel Isocyanate-Derived Metabolites of the Formamide N-Formylamphetamine with the Combined Use of Electrospray Mass Spectrometry and Stable Isotope Methodology

  摘要：

  Bioactivation of the formamide N-formylamphetamine (NFA) to 1-methyl-2-phenylethyl isocyanate (MPIC) was investigated in rats by screening bile and urine for conjugates subsequent to the phase I event. NFA was administered to rats as a mixture of protio- and pentadeuteriophenyl analogues to gain insight into the carbamoylating activity of MPIC when traced by electrospray liquid chromatography/mass spectrometry (LC/MS). An LC/MS contour generated by recording the summed mass spectrum as a function of chromatographic retention time allowed four biliary metabolites to be identified from four sets of doublets, with the peak of each doublet offset by 5 amu and ca. 0.07 min. Tandem mass spectrometry experiments allowed these metabolites to be attributed structurally to the glutathione, cysteinylglycine, cysteine, and N-acetylcysteine conjugates of the isocyanate MPIC. These assignments were subsequently validated by comparison of the LC/MS properties of the metabolites to synthetic reference compounds. Only the carbamoylated N-acetylcysteine conjugate was detected in urine. The observed excretion in bile of all metabolites of the mercapturate pathway is novel for formamide metabolism. NFA can thus be added to the short list of compounds that are eliminated in this fashion. Factors envisioned as contributory to this metabolic profile in bile include hepatorenal, enterohepatic, and biliary-hepatic cycling, in addition to possible equilibrium exchange of the isocyanate from thiocarbamate conjugates to endogenous free thiols during the course of biliary transit.

  DOI：

  10.1021/tx00048a010
• 作为产物：
  描述：

  对硝基苯酚 在 sodium carbonate 、 N,N-二甲基苯胺 、 三乙胺 作用下， 以 氯仿 为溶剂， 生成 4'-nitrophenyl (1-methyl-2-phenylethyl)carbamate
  参考文献：
  名称：

  生理活性胺的氨基甲酸酯潜伏作用。

  摘要：

  DOI：

  10.1021/jm00300a035