N-benzyloxycarbonyl-S-(2,4-dinitrophenyl)glutathione | 277310-62-0

• 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-benzyloxycarbonyl-S-(2,4-dinitrophenyl)glutathione
• CAS: 277310-62-0
• 化学式: C₂₄H₂₅N₅O₁₂S
• 分子量: 607.555
• InChiKey: UTRRCCBZDPMMBZ-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  42.0
• 可旋转键数：
  16.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  257.41
• 氢给体数：
  5.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  4-甲基-2-戊醇 、 N-benzyloxycarbonyl-S-(2,4-dinitrophenyl)glutathione 在 氯化亚砜 作用下， 以63%的产率得到N-benzyloxycarbonyl-S-(2,4-dinitrophenyl)glutathione di-4-methyl-2-pentyl ester
  参考文献：
  名称：

  QSAR Study on the Contribution of Log P and E_s to the in Vitro Antiprotozoal Activity of Glutathione Derivatives

  摘要：

  A series of N-S-blocked glutathione monoester and diester derivatives based on N-benzyloxy-carbonyl-S-(2,4-dinitrophenyl)glutathione were evaluated for activity against the pathogenic parasites Trypanosoma brucei brucei, Trypanosoma cruzi, and Leishmania donovani in vitro. Only monoesters 7-9 with a log P value of >2.7 were active inhibitors of Tb. brucei bloodstream form trypomastigotes. Diester compounds 10-15 and 17-27 in most cases were better inhibitors of TA brucei than monoester compounds, and some displayed high activity against T. cruzi 14 and L. donovani 17, 19, 29. Compounds 14, 24, and 25 were the most active compounds identified against Tb. brucei having ED50 values of <0.4 muM. Analysis of the inhibition data (ED50) vs calculated log P and E-s values provided evidence to support membrane penetration and steric factors as the key component in the activity of these compounds. The optimum values for log P and E-s determined were 5.8 and -0.70, respectively. A QSAR equation relating log(1/ED50) vs log P and E-s was determined and interpreted within the proposed mechanism of activity for these compounds.

  DOI：

  10.1021/jm000502n
• 作为产物：
  描述：

  S-(2,4二硝基苯基)-谷胱甘肽 、 氯甲酸苄酯 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以90%的产率得到N-benzyloxycarbonyl-S-(2,4-dinitrophenyl)glutathione
  参考文献：
  名称：

  QSAR Study on the Contribution of Log P and E_s to the in Vitro Antiprotozoal Activity of Glutathione Derivatives

  摘要：

  A series of N-S-blocked glutathione monoester and diester derivatives based on N-benzyloxy-carbonyl-S-(2,4-dinitrophenyl)glutathione were evaluated for activity against the pathogenic parasites Trypanosoma brucei brucei, Trypanosoma cruzi, and Leishmania donovani in vitro. Only monoesters 7-9 with a log P value of >2.7 were active inhibitors of Tb. brucei bloodstream form trypomastigotes. Diester compounds 10-15 and 17-27 in most cases were better inhibitors of TA brucei than monoester compounds, and some displayed high activity against T. cruzi 14 and L. donovani 17, 19, 29. Compounds 14, 24, and 25 were the most active compounds identified against Tb. brucei having ED50 values of <0.4 muM. Analysis of the inhibition data (ED50) vs calculated log P and E-s values provided evidence to support membrane penetration and steric factors as the key component in the activity of these compounds. The optimum values for log P and E-s determined were 5.8 and -0.70, respectively. A QSAR equation relating log(1/ED50) vs log P and E-s was determined and interpreted within the proposed mechanism of activity for these compounds.

  DOI：

  10.1021/jm000502n