5-Hept-1-ynyl-1-(2-hydroxy-ethoxymethyl)-1H-pyrimidine-2,4-dione | 848609-25-6

• 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: 5-Hept-1-ynyl-1-(2-hydroxy-ethoxymethyl)-1H-pyrimidine-2,4-dione
• 英文别名: 5-Hept-1-ynyl-1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
• CAS: 848609-25-6
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: HKQOLURKIIFDNM-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Hept-1-ynyl-1-(2-hydroxy-ethoxymethyl)-1H-pyrimidine-2,4-dione 在 copper(l) iodide 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以108 mg的产率得到3-(2-Hydroxy-ethoxymethyl)-6-pentyl-3H-furo[2,3-d]pyrimidin-2-one
  参考文献：
  名称：

  Studies on acyclic pyrimidines as inhibitors of mycobacteria

  摘要：

  In vitro anti-mycobacterial activities of several 5-substituted acyclic pyrimidine nucleosides containing 1-(2-hydroxyethoxy)methyl and 1-[(2-h),droxy-1-(hydroxymethyl) ethoxy)methyl] acyclic moieties are investigated against three mycobacteria viz, Mycobacterium tuberculosis. Mycobacterium bovis, and Mycobacterium avium, which cause serious infections and mortality in healthy people as well as patients with AIDS. 1-(2-Hydroxyethoxy)methyl-5-(1-azido-2-haloethyl or I-azidovinyl) analogs (4-7), 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl]-5-decynyluracil (37), and 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl]-5-dodecynyluracil (38) exhibited significant in vitro anti-tubercular activity against these mycobacteria. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.032
• 作为产物：
  描述：

  1-(2-acetoxyethoxymethyl)-uracil 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 ammonium cerium(IV) nitrate 、 碘 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 1.0h， 生成 5-Hept-1-ynyl-1-(2-hydroxy-ethoxymethyl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  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及抗病毒活性。

  摘要：

  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。

  DOI：

  10.1016/j.bmc.2004.11.057

文献信息

• 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。
• Studies on acyclic pyrimidines as inhibitors of mycobacteria
  作者：Naveen C. Srivastav、Tracey Manning、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1016/j.bmc.2006.12.032

  日期：2007.3

  In vitro anti-mycobacterial activities of several 5-substituted acyclic pyrimidine nucleosides containing 1-(2-hydroxyethoxy)methyl and 1-[(2-h),droxy-1-(hydroxymethyl) ethoxy)methyl] acyclic moieties are investigated against three mycobacteria viz, Mycobacterium tuberculosis. Mycobacterium bovis, and Mycobacterium avium, which cause serious infections and mortality in healthy people as well as patients with AIDS. 1-(2-Hydroxyethoxy)methyl-5-(1-azido-2-haloethyl or I-azidovinyl) analogs (4-7), 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl]-5-decynyluracil (37), and 1-[(2-hydroxy-1-(hydroxymethyl)ethoxy)methyl]-5-dodecynyluracil (38) exhibited significant in vitro anti-tubercular activity against these mycobacteria. (c) 2006 Elsevier Ltd. All rights reserved.