N-(2-chloro-1,1-dideuterioethyl)-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-amine | 433709-07-0

• 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-1,1-dideuterioethyl)-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-amine
• CAS: 433709-07-0
• 化学式: C₅H₁₂ClN₂O₂P
• 分子量: 200.573
• InChiKey: DZKGMGPLDJOVCX-APZFVMQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-chloro-1,1-dideuterioethyl)-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-amine 在 硼氘化钠 、 三氟化硼乙醚 、 三乙胺盐酸盐 作用下， 生成 N,3-bis(2-chloro-1,1-dideuterioethyl)-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
  参考文献：
  名称：

  Studies on the Side-chain Hydroxylation of Ifosfamide and Its Bromo Analogue

  摘要：

  Deutero-substituted (alpha,alpha,alpha',alpha'-tetradeuterated) derivatives of ifosfamide (IF-d(4)) and its bromo analogue were synthesised. In vitro metabolic studies showed that microsomal hydroxylation of IF-d(4) is slower than for unlabelled compound, suggesting that kinetic isotope effect operates during those transformations. At the same time deutero-substituted derivatives are more active against L1210 leukaemia in mice than unlabelled compounds, suggesting a negative role of side-chain hydroxylation metabolic pathways in the anticancer activity of ifosfamide and its analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00768-5
• 作为产物：
  描述：

  N-(2-chloro-1,1-dideuterioethyl)-2-oxido-3-(1-phenylethyl)-1,3,2-oxazaphosphinan-2-ium-2-amine 在 palladium on activated charcoal 氢气 作用下， 生成 N-(2-chloro-1,1-dideuterioethyl)-2-oxido-1,3,2-oxazaphosphinan-2-ium-2-amine
  参考文献：
  名称：

  Studies on the Side-chain Hydroxylation of Ifosfamide and Its Bromo Analogue

  摘要：

  Deutero-substituted (alpha,alpha,alpha',alpha'-tetradeuterated) derivatives of ifosfamide (IF-d(4)) and its bromo analogue were synthesised. In vitro metabolic studies showed that microsomal hydroxylation of IF-d(4) is slower than for unlabelled compound, suggesting that kinetic isotope effect operates during those transformations. At the same time deutero-substituted derivatives are more active against L1210 leukaemia in mice than unlabelled compounds, suggesting a negative role of side-chain hydroxylation metabolic pathways in the anticancer activity of ifosfamide and its analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00768-5

文献信息

• Studies on the Side-chain Hydroxylation of Ifosfamide and Its Bromo Analogue
  作者：Konrad Misiura、Ryszard W. Kinas、Halina Kuśnierczyk

  DOI：10.1016/s0960-894x(01)00768-5

  日期：2002.2

  Deutero-substituted (alpha,alpha,alpha',alpha'-tetradeuterated) derivatives of ifosfamide (IF-d(4)) and its bromo analogue were synthesised. In vitro metabolic studies showed that microsomal hydroxylation of IF-d(4) is slower than for unlabelled compound, suggesting that kinetic isotope effect operates during those transformations. At the same time deutero-substituted derivatives are more active against L1210 leukaemia in mice than unlabelled compounds, suggesting a negative role of side-chain hydroxylation metabolic pathways in the anticancer activity of ifosfamide and its analogues. (C) 2002 Elsevier Science Ltd. All rights reserved.