1-[(3R,5R)-3-(hydroxymethyl)-2-methyl-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(3R,5R)-3-(hydroxymethyl)-2-methyl-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
• 化学式: C₁₀H₁₅N₃O₄
• 分子量: 241.247
• InChiKey: WYRDYZBRXPIFQR-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  82.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3R,5R)-3-(hydroxymethyl)-2-methyl-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 diethyl {(1'RS,4'RS)-1'-[[(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)]-3'-methyl-2'-oxa-3'-aza-cyclopent-4'-yl]}methylphosphonate
  参考文献：
  名称：

  Phosphonated Carbocyclic 2‘-Oxa-3‘-azanucleosides as New Antiretroviral Agents

  摘要：

  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.

  DOI：

  10.1021/jm070285r
• 作为产物：
  描述：

  1-[(1'RS,4'RS)-(4'-((tert-butyldiphenylsilyloxy)methyl)-3'-methyl)-2'-oxa-3'-azacyclopent-1'-yl]-5-methylpyrimidine-2,4-(1H,3H)-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-[(3R,5R)-3-(hydroxymethyl)-2-methyl-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  NO二杂环核苷：2' - n-甲基-3'-羟甲基-1'，2'-异恶唑啉基胸苷的合成

  摘要：

  异恶唑烷胸腺嘧啶衍生物是通过甲硅烷基化的胸腺嘧啶与乙酸异恶唑烷基酯的缩合反应合成的，该方法是将α，β-不饱和酯与N-甲基羟胺进行迈克尔加成反应，然后进行DIBAL还原和乙酸酯生产。

  DOI：

  10.1016/0040-4039(95)01499-8

文献信息

• N-O diheterocyclic nucleosides: Synthesis of 2′-n-methyl-3′-hydroxymethyl-1′,2′-isoxazolidinylthymidine
  作者：Yuejun Xiang、Jie Chen、Raymond F. Schinazi、Kang Zhao

  DOI：10.1016/0040-4039(95)01499-8

  日期：1995.10

  Isoxazolidine thymidine derivatives were synthesized by the condensation of silylated thymine with isoxazolidinyl acetate prepared by the Michael addition of an α,β-unsaturated ester with N-methylhydroxyamine followed by DIBAL reduction and acetate production.

  异恶唑烷胸腺嘧啶衍生物是通过甲硅烷基化的胸腺嘧啶与乙酸异恶唑烷基酯的缩合反应合成的，该方法是将α，β-不饱和酯与N-甲基羟胺进行迈克尔加成反应，然后进行DIBAL还原和乙酸酯生产。
• 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.