N-(2-chloro-2,2-dimethylethyl)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂膦
• 英文名称: N-(2-chloro-2,2-dimethylethyl)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
• 英文别名: 3-(2-chloroethyl)-N-(2-chloro-2-methylpropyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine；3-(2-chloroethyl)-N-(2-chloro-2-methylpropyl)-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine
• 化学式: C₉H₁₉Cl₂N₂O₂P
• 分子量: 289.142
• InChiKey: JYRKQJGYOINGHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(2,2-Dimethyl-aziridin-1-yl)-[1,3,2]oxazaphosphinane 2-oxide 在 盐酸 、 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.5h， 生成 N-(2-chloro-2,2-dimethylethyl)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
  参考文献：
  名称：

  Synthesis, in vitro metabolic studies, and antitumour activity of methyl analogues of ifosfamide

  摘要：

  Synthesis of 2-chloro-1,1-dimethylethyl and 2-chloro-2,2-dimethylethyl analogues of ifosfamide was performed via aziridine intermediate. In vitro metabolic activation showed that both compounds are metabolised at a rate similar to the parent drug. However, their anticancer activity against L1210 leukaemia in mice was lower as compared with ifosfamide. The reduction of antitumour efficiency of examined analogues is probably caused by a lower ability to cross-link DNA by their final, active metabolites.

  DOI：

  10.1002/1521-4184(200109)334:8/9<291::aid-ardp291>3.0.co;2-j

文献信息

• Synthesis, in vitro metabolic studies, and antitumour activity of methyl analogues of ifosfamide
  作者：Konrad Misiura、Karina Kardacka、Halina Kusnierczyk

  DOI：10.1002/1521-4184(200109)334:8/9<291::aid-ardp291>3.0.co;2-j

  日期：2001.9

  Synthesis of 2-chloro-1,1-dimethylethyl and 2-chloro-2,2-dimethylethyl analogues of ifosfamide was performed via aziridine intermediate. In vitro metabolic activation showed that both compounds are metabolised at a rate similar to the parent drug. However, their anticancer activity against L1210 leukaemia in mice was lower as compared with ifosfamide. The reduction of antitumour efficiency of examined analogues is probably caused by a lower ability to cross-link DNA by their final, active metabolites.