N,N:N',N'-bis(1,2-ethanediyl)-N"-{[(2,2,6,6-tetramethylpiperidin-4-yl)amino]carbonyl}phosphoric triamide | 96662-66-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N,N:N',N'-bis(1,2-ethanediyl)-N"-{[(2,2,6,6-tetramethylpiperidin-4-yl)amino]carbonyl}phosphoric triamide
• 英文别名: 1-[Bis(aziridin-1-yl)phosphoryl]-3-(2,2,6,6-tetramethylpiperidin-4-yl)urea
• CAS: 96662-66-7
• 化学式: C₁₄H₂₈N₅O₂P
• 分子量: 329.382
• InChiKey: JJMNXMOJHOPTDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  76.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,6,6-四甲基哌啶胺 、 乌瑞替派 以 甲苯 为溶剂， 反应 0.5h， 以80%的产率得到N,N:N',N'-bis(1,2-ethanediyl)-N"-{[(2,2,6,6-tetramethylpiperidin-4-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

• SOSNOVSKY G.; RAO N. UMA MAHESWARA; LI SHU WEN, J. MED. CHEM., 29,(1986) N 11, 2225-2230
  作者：SOSNOVSKY G.、 RAO N. UMA MAHESWARA、 LI SHU WEN

  DOI：——

  日期：——
• 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.