四氢-N-(2-溴乙基)-3-(2-氯乙基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物 | 104149-14-6

• 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
• 中文名称: 四氢-N-(2-溴乙基)-3-(2-氯乙基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物
• 英文名称: N-(2-bromoethyl)-3-(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-oxide
• 英文别名: 2-(2-bromoethylamino)-2-oxo-3-(2-chloroethyl)-1.3.2-oxazaphosphorinane；bromofosfamide；N-(2-bromoethyl)-3-(2-chloroethyl)-2-oxo-1,3,2λ5-oxazaphosphinan-2-amine
• CAS: 104149-14-6
• 化学式: C₇H₁₅BrClN₂O₂P
• 分子量: 305.539
• InChiKey: ZJVAVRRLTFVZIP-UHFFFAOYSA-N

物化性质

• 熔点：
  59-60 °C
• 沸点：
  349.7±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 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

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  异环磷酰胺 在 氢溴酸 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 0.25h， 生成 四氢-N-(2-溴乙基)-3-(2-氯乙基)-2H-1,3,2-氧杂氮杂磷杂苯-2-胺2-氧化物
  参考文献：
  名称：

  Synthesis and antitumor activity of analogs of ifosfamide modified in the N-(2-chloroethyl) group

  摘要：

  A series of 3-(2-chloroethyl)-N-(2-X-ethyl)tetrahydro-2H-1,3,2-oxazaphosphorin -2-amine 2-oxides with various X substituents have been prepared by cyclization of racemic ifosfamide or its enantiomers with sodium hydride and subsequent treatment of intermediary products with hydrobromic acid, diethyl hydrogen phosphate, dibenzyl hydrogen phosphate, p-toluenesulfonic acid, and acetic acid. All of these compounds were tested in vivo against L 1210 lymphoid leukemia in mice. Only bromo analogue 13 and its enantiomers were effective, exceeding the activity of racemic ifosfamide and cyclophosphamide. The therapeutic index of the racemic 13 and its levorotatory enantiomer was about 1.7 times higher than that for ifosfamide and about 2.7 times higher than that for cyclophosphamide.

  DOI：

  10.1021/jm00396a036

文献信息

• STEC, WOJCIECH JACEK;W.;KINAS, RYSZARD W.;MISIURA, KONRAD
  作者：STEC, WOJCIECH JACEK、W.、KINAS, RYSZARD W.、MISIURA, KONRAD

  DOI：——

  日期：——
• MISIURA, KONRAD;KINAS, RYSZARD W.;STEC, WOJCIECH J.;KUSNIERCZYK, HALINA;R+, J. MED. CHEM., 31,(1988) N 1, 226-230
  作者：MISIURA, KONRAD、KINAS, RYSZARD W.、STEC, WOJCIECH J.、KUSNIERCZYK, HALINA、R+

  DOI：——

  日期：——
• US4684742A
  申请人：——

  公开号：US4684742A

  公开（公告）日：1987-08-04
• Synthesis and antitumor activity of analogs of ifosfamide modified in the N-(2-chloroethyl) group
  作者：Konrad Misiura、Ryszard W. Kinas、Wojciech J. Stec、Halina Kusnierczyk、Czeslaw Radzikowski、Akio Sonoda

  DOI：10.1021/jm00396a036

  日期：1988.1

  A series of 3-(2-chloroethyl)-N-(2-X-ethyl)tetrahydro-2H-1,3,2-oxazaphosphorin -2-amine 2-oxides with various X substituents have been prepared by cyclization of racemic ifosfamide or its enantiomers with sodium hydride and subsequent treatment of intermediary products with hydrobromic acid, diethyl hydrogen phosphate, dibenzyl hydrogen phosphate, p-toluenesulfonic acid, and acetic acid. All of these compounds were tested in vivo against L 1210 lymphoid leukemia in mice. Only bromo analogue 13 and its enantiomers were effective, exceeding the activity of racemic ifosfamide and cyclophosphamide. The therapeutic index of the racemic 13 and its levorotatory enantiomer was about 1.7 times higher than that for ifosfamide and about 2.7 times higher than that for cyclophosphamide.