diethyl 2-[methyl(oxido)imino]ethylphosphonate | 849244-25-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diethyl 2-[methyl(oxido)imino]ethylphosphonate
• CAS: 849244-25-3；863408-55-3
• 化学式: C₇H₁₆NO₄P
• 分子量: 209.182
• InChiKey: RTHBJQSEHNADOC-UHFFFAOYSA-N

物化性质

• 沸点：
  377.6±21.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  13.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  61.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diethyl 2-[methyl(oxido)imino]ethylphosphonate 在 potassium carbonate 、 牛血清白蛋白 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 34.25h， 生成 diethyl [(1'SR,4'RS)-1'-(4-amino-2-oxopyrimidin-1(2H)-yl)-3'-methyl-2'-oxa-3'-aza-cyclopent-4'-yl]methylphosphonate
  参考文献：
  名称：

  Synthesis of Phosphonated Carbocyclic 2‘-Oxa-3‘-aza-nucleosides:  Novel Inhibitors of Reverse Transcriptase

  摘要：

  Phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides have been synthesized in good yields by 1,3-dipolar cycloaddition methodology. The cytotoxicity and the reverse transcriptase inhibitory activity of the obtained compounds have been investigated. Phosphonated carbocyclic 2'-oxa-3'-aza-nucleosides, while showing low levels of cytotoxicity, exert a specific inhibitor activity on two different reverse transcriptases, which is comparable with that of AZT, opening new perspectives on their possible use as therapeutic agents, in anti-retroviral and anti-HBV chemotherapy.

  DOI：

  10.1021/jm049399i
• 作为产物：
  描述：

  N-甲基羟胺 、 (甲酰基甲基)磷酸二乙酯 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 diethyl 2-[methyl(oxido)imino]ethylphosphonate
  参考文献：
  名称：

  [EN] NUCLEOSIDE ANALOGUES WITH ANTIVIRAL ACTIVITY
  [FR] ANALOGUES DE NUCLEOSIDES A ACTIVITE ANTIVIRALE

  摘要：

  本文描述了具有抗病毒活性的式（I）的核苷类似物；它们的制备过程，以及它们在制备对治疗病毒病变有用的药物组合物中的用途。

  公开号：

  WO2005082896A1

文献信息

• Phosphonated Carbocyclic 2‘-Oxa-3‘-azanucleosides as New Antiretroviral Agents
  作者：Ugo Chiacchio、Antonio Rescifina、Daniela Iannazzo、Anna Piperno、Roberto Romeo、Luisa Borrello、Maria Teresa Sciortino、Emanuela Balestrieri、Beatrice Macchi、Antonio Mastino、Giovanni Romeo

  DOI：10.1021/jm070285r

  日期：2007.7.1

  Phosphonated carbocyclic 2'-oxa-3'-azanucleosides have been synthesized and tested for their antiretroviral activity. The obtained results have shown that some of the compounds were as powerful as azydothymidine in inhibiting the reverse transcriptase activity of the human retrovirus T-cell leukemia/lymphotropic virus type 1 and in protecting human peripheral blood mononuclear cells against human retrovirus T-cell leukemia/lymphotropic virus type 1 transmission in vitro. These data indicate that phosphonated carbocyclic 2'-oxa-3'-azanucleosides possess the necessary requirements to efficiently counteract infections caused by human retroviruses.