N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N''-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide | 103981-93-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N''-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide
• 英文别名: N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N"-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide
• CAS: 103981-93-7
• 化学式: C₁₇H₃₃N₅O₃P
• 分子量: 386.454
• InChiKey: YODZWVQNFSXLLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.56
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  87.36
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N''-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide 在 sodium ascorbate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以58%的产率得到N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N"-<<(2,2,5,5-tetramethyl-1-hydroxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide
  参考文献：
  名称：

  In the search for new anticancer drugs. 19. A predictive design of N,N:N',N':N",N"-tri-1,2-ethanediylphosphoric triamide (TEPA) analogues

  摘要：

  The nitroxyl-labeled analogues of N,N:N',N':N",N"-tri-1,2-ethanediylphosphoric triamide (TEPA), N,N:N',N'-bis(1,2-ethanediyl)-N"-[[(2,2,6,6-tetramethyl-1-oxypiperidi n-4- yl)amino]carbonyl]phosphoric triamide (5a) and N,N:N',N'-bis(1,2-ethanediyl)-N"-[[(2,2,5,5-tetramethyl-1-oxypyrrolid in-3- yl)amino]carbonyl]phosphoric triamide (11a), possess therapeutic indexes that are 8-12 times higher than those of thio-TEPA (1) and TEPA (2). The introduction of methyl groups into the aziridine ring, or the replacement of the nitroxyl moiety with hydroxylamine or amine derivatives, or with an adamantane moiety, results in compounds of lesser activity. An attempt is made to rationalize these results using a lipophilicity scale. A predictive design pattern is established.

  DOI：

  10.1021/jm00161a016
• 作为产物：
  描述：

  3-氨基-2,2,5,5-四甲基-1-吡咯烷酮 、 N,N-bis(2,2-dimethylaziridinyl)phosphorylurethane 以 甲苯 为溶剂， 反应 0.5h， 以33%的产率得到N,N:N',N'-bis(2-methyl-1,2-propanediyl)-N''-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide
  参考文献：
  名称：

  In the search for new anticancer drugs. 19. A predictive design of N,N:N',N':N",N"-tri-1,2-ethanediylphosphoric triamide (TEPA) analogues

  摘要：

  The nitroxyl-labeled analogues of N,N:N',N':N",N"-tri-1,2-ethanediylphosphoric triamide (TEPA), N,N:N',N'-bis(1,2-ethanediyl)-N"-[[(2,2,6,6-tetramethyl-1-oxypiperidi n-4- yl)amino]carbonyl]phosphoric triamide (5a) and N,N:N',N'-bis(1,2-ethanediyl)-N"-[[(2,2,5,5-tetramethyl-1-oxypyrrolid in-3- yl)amino]carbonyl]phosphoric triamide (11a), possess therapeutic indexes that are 8-12 times higher than those of thio-TEPA (1) and TEPA (2). The introduction of methyl groups into the aziridine ring, or the replacement of the nitroxyl moiety with hydroxylamine or amine derivatives, or with an adamantane moiety, results in compounds of lesser activity. An attempt is made to rationalize these results using a lipophilicity scale. A predictive design pattern is established.

  DOI：

  10.1021/jm00161a016