N,N:N',N'-bis(1,2-ethanediyl)-N"-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide | 103981-99-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: N,N:N',N'-bis(1,2-ethanediyl)-N"-<<(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino>carbonyl>phosphoric triamide
• 英文别名: N,N:N',N'-bis(1,2-ethanediyl)-N"-{[(2,2,5,5-tetramethyl-1-oxypyrrolidin-3-yl)amino]carbonyl}phosphoric triamide
• CAS: 103981-99-3
• 化学式: C₁₃H₂₅N₅O₃P
• 分子量: 330.347
• InChiKey: ZXHGQJXDFCILDM-UHFFFAOYSA-N

物化性质

• 熔点：
  122.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  68.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N,N:N',N'-bis(1,2-ethanediyl)-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62%的产率得到N,N:N',N'-bis(1,2-ethanediyl)-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：

  乌瑞替派 、 3-氨基-2,2,5,5-四甲基-1-吡咯烷酮 以 甲苯 为溶剂， 反应 0.5h， 以44%的产率得到N,N:N',N'-bis(1,2-ethanediyl)-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

文献信息

• 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
  作者：George Sosnovsky、N. Uma Maheswara Rao、Shu Wen Li

  DOI：10.1021/jm00161a016

  日期：1986.11

  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.