3-N-[2-(acetoxy)ethoxymethyl]-6-octyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one | 825634-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃[2,3-d]嘧啶
• 英文名称: 3-N-[2-(acetoxy)ethoxymethyl]-6-octyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
• 英文别名: 2-((6-Octyl-2-oxofuro[2,3-d]pyrimidin-3(2H)-yl)methoxy)ethyl acetate；2-[(6-octyl-2-oxofuro[2,3-d]pyrimidin-3-yl)methoxy]ethyl acetate
• CAS: 825634-75-1
• 化学式: C₁₉H₂₈N₂O₅
• 分子量: 364.442
• InChiKey: LXLYIVAHBNPASP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-N-[2-(acetoxy)ethoxymethyl]-6-octyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 Furo[2,3-d]pyrimidin-2(3H)-one, 3-[(2-hydroxyethoxy)methyl]-6-octyl-
  参考文献：
  名称：

  AgNO3催化取代呋喃嘧啶核苷的高效制备

  摘要：

  描述了一种合成取代的呋喃并嘧啶核苷的有效方法。用催化 AgNO3 处理后，5-炔基尿嘧啶衍生物几乎定量转化为相应的双环核苷类似物。

  DOI：

  10.1055/s-2004-831330
• 作为产物：
  描述：

  1-癸炔 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 silver nitrate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 3-N-[2-(acetoxy)ethoxymethyl]-6-octyl-2,3-dihydrofuro[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  AgNO3催化取代呋喃嘧啶核苷的高效制备

  摘要：

  描述了一种合成取代的呋喃并嘧啶核苷的有效方法。用催化 AgNO3 处理后，5-炔基尿嘧啶衍生物几乎定量转化为相应的双环核苷类似物。

  DOI：

  10.1055/s-2004-831330

文献信息

• Highly Efficient AgNO₃-Catalyzed Preparation of Substituted Furano­pyrimidine Nucleosides
  作者：Luigi A. Agrofoglio、Vincent Aucagne、Franck Amblard

  DOI：10.1055/s-2004-831330

  日期：——

  An efficient method for the synthesis of substituted ­furanopyrimidine nucleosides is described. Upon treatment with catalytic AgNO3, 5-alkynyl uracil derivatives were almost quanti­tatively converted into their corresponding bicyclic nucleoside ­analogues.

  描述了一种合成取代的呋喃并嘧啶核苷的有效方法。用催化 AgNO3 处理后，5-炔基尿嘧啶衍生物几乎定量转化为相应的双环核苷类似物。
• Synthesis and Biological Evaluation of Acyclic 3-[(2-Hydroxyethoxy)methyl] Analogues of Antiviral Furo- and Pyrrolo[2,3-<i>d</i>]pyrimidine Nucleosides
  作者：Zlatko Janeba、Jan Balzarini、Graciela Andrei、Robert Snoeck、Erik De Clercq、Morris J. Robins

  DOI：10.1021/jm050291s

  日期：2005.7.1

  The remarkably potent and specific activity against varicella-zoster virus (VZV) shown by 2'deoxymicleosides of furo[2,3-d]pyrimidin-2(3H)-one and related ring systems is dependent on key structural features including the length and nature of the side-chain at C6 and the structure and stereochemistry of the sugar moiety at N3. Removal of the X-hydroxyl group from potent anti-VZV 2'-deoxynucleosides results in loss of the VZV activity, but such 2',3'-dideoxynucleoside analogues have shown anti-HCMV activity. We now report acyclic analogues with comparable side-chains at C6, but with the sugar moiety at N3 replaced with the (2-hydroxyethoxy)methyl group (present in the antiherpes drug acyclovir). Examples of both furo[2,3, d]-and pyrrolo[2,3-d]pyrimidin-2(3H)-one acyclic analogues were prepared and evaluated in a number of virus infected cells and in tumor cell cultures. Certain of the long-chain analogues showed activity against VZV and HCMV. No significant activity against other DNA and RNA virus replication or against tumor cell proliferation was observed.
• Synthesis and antiviral activity of novel acyclic nucleosides in the 5-alkynyl- and 6-alkylfuro[2,3-d]pyrimidine series
  作者：Franck Amblard、Vincent Aucagne、Pierre Guenot、Raymond F. Schinazi、Luigi A. Agrofoglio

  DOI：10.1016/j.bmc.2004.11.057

  日期：2005.2

  The synthesis of novel acyclic nucleosides in the 5-alkynyl and 6-alkylfuro[2,3-d]pyrimidine series is described. These compounds were evaluated against HIV and HSV in order to determine their spectrum of antiviral activity. Their cytotoxicities against PBM, CEM and VERO cells were also determined. Compounds 21d and 24b displayed moderate EC50s of 2.7 and 4.9 microM, respectively, against HIV-1 and

  描述了5-炔基和6-烷基呋喃[2,3-d]嘧啶系列中新型无环核苷的合成。对这些化合物针对HIV和HSV进行了评估，以确定它们的抗病毒活性谱。还确定了它们对PBM，CEM和VERO细胞的细胞毒性。化合物21d和24b对HIV-1的中度EC50分别为2.7和4.9 microM，对HSV的中度EC50分别为6.3和4.8 microM。然而，这些化合物还显示出细胞毒性，表明抗病毒作用是继毒作用之后的。