5-iodo-1-[2-(2-phenyl-1,3-dioxan-5-yliden)ethyl]-2,4(1H,3H)-pyrimidinedione | 839674-90-7

• 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-iodo-1-[2-(2-phenyl-1,3-dioxan-5-yliden)ethyl]-2,4(1H,3H)-pyrimidinedione
• CAS: 839674-90-7
• 化学式: C₁₆H₁₅IN₂O₄
• 分子量: 426.211
• InChiKey: NHDKGROHBOOVEN-WDZFZDKYSA-N

物化性质

• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.32
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-iodo-1-[2-(2-phenyl-1,3-dioxan-5-yliden)ethyl]-2,4(1H,3H)-pyrimidinedione 在 palladium diacetate 、 三苯胂 、 potassium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[4-hydroxy-3-(hydroxymethyl)-2-butenyl]-5-(2-thienyl)-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

  摘要：

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.019
• 作为产物：
  描述：

  5-methylene-2-phenyl-[1,3]dioxolane 、 1-allyl-5-iodo-1H-pyrimidine-2,4-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以57%的产率得到5-iodo-1-[2-(2-phenyl-1,3-dioxan-5-yliden)ethyl]-2,4(1H,3H)-pyrimidinedione
  参考文献：
  名称：

  Efficient synthesis of various acycloalkenyl derivatives of pyrimidine using cross-metathesis and Pd(0) methodologies

  摘要：

  Novel acyclonucleosides (9a-d, 10a-d, 18a,b and 19a,b) have been prepared using Pd(0) and cross-metathesis methodologies. The allylic N-alkylation under Tsuji-Trost conditions was used to introduce the nucleobase, while the Suzuki-Miyaura reaction afforded C-5 substituted uracil analogues. The cross-metathesis performed with a ruthenium catalyst was used to provide new acycloalkenyl nucleosides. The antiviral activities of all final compounds have been evaluated. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.11.019

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。