5-ethoxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine | 56145-29-0

• 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-ethoxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine
• 英文别名: Pyrimidine, 5-(ethoxymethyl)-2,4-bis[(trimethylsilyl)oxy]-；[5-(ethoxymethyl)-2-trimethylsilyloxypyrimidin-4-yl]oxy-trimethylsilane
• CAS: 56145-29-0
• 化学式: C₁₃H₂₆N₂O₃Si₂
• 分子量: 314.532
• InChiKey: ZEDUNKZVJUPVLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  53.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-ethoxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.5h， 生成 1-(3-azido-2,3-dideoxy-β-D-erythro-pentofuranosyl)-5-ethoxymethyluracil
  参考文献：
  名称：

  5-Alkoxymethyl-3'-azido-2', 3'-dideoxyuridines 的合成及抗 HIV 活性

  摘要：

  甲基3-叠氮基-5-O-叔丁基二苯基甲硅烷基-2,3-双脱氧-D-赤型-呋喃糖苷(3)与甲硅烷基化的5-羟甲基尿嘧啶(1a)及其C1-C6烷基醚1b-g偶联得到相应的受保护核苷 4a-g 用 Bu4NF 脱保护，得到 3-叠氮核苷 5a-g 和 6a-g。α-端基异构体 6f、g 对 HIV 表现出中等活性。未发现化合物 5 和 6 对 HSV-1 具有显着活性。

  DOI：

  10.1002/ardp.19933260702
• 作为产物：
  描述：

  5-(氯甲基)尿嘧啶 在 硫酸氢铵 作用下， 反应 8.0h， 生成 5-ethoxymethyl-2,4-bis-trimethylsilanyloxy-pyrimidine
  参考文献：
  名称：

  Synthesis of various 5-alkoxymethyluracil analogues and structure–cytotoxic activity relationship study

  摘要：

  A number of 5-alkoxymethyluracil analogues were synthesized to evaluate their cytotoxic activity. 5-Alkoxymethyluracil derivatives 1 were prepared via known nucleophilic substitution of 5-chloromethyluracil 5 and subsequently transformed to their corresponding nucleosides 2. All prepared compounds were submitted to cytotoxic activity testing against drug sensitive and drug resistant leukaemia cells and solid tumour derived cell lines. In addition, the cytotoxic activity of 5-alkoxymethyluracil analogues 1 and 2 was compared with the previously published 5-[alkoxy(4-nitrophenyl)methyl]uracil analogues 3 and 4. Extensive structure-cytotoxic activity relationship studies are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.07.026

文献信息

• Synthesis of various 5-alkoxymethyluracil analogues and structure–cytotoxic activity relationship study
  作者：Lucie Brulíková、Petr Džubák、Marián Hajdúch、Jan Hlaváč

  DOI：10.1016/j.carres.2011.07.026

  日期：2011.10

  A number of 5-alkoxymethyluracil analogues were synthesized to evaluate their cytotoxic activity. 5-Alkoxymethyluracil derivatives 1 were prepared via known nucleophilic substitution of 5-chloromethyluracil 5 and subsequently transformed to their corresponding nucleosides 2. All prepared compounds were submitted to cytotoxic activity testing against drug sensitive and drug resistant leukaemia cells and solid tumour derived cell lines. In addition, the cytotoxic activity of 5-alkoxymethyluracil analogues 1 and 2 was compared with the previously published 5-[alkoxy(4-nitrophenyl)methyl]uracil analogues 3 and 4. Extensive structure-cytotoxic activity relationship studies are reported. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and Anti-HIV Activity of 5-Alkoxymethyl-3′-azido-2′,3′-dideoxyuridines
  作者：Ahmed E.-S. Abdel-Megied、Poul Hansen、Erik B. Pedersen、Claus Nielsen、Carsten M. Nielsen

  DOI：10.1002/ardp.19933260702

  日期：——

  Methyl 3‐azido‐5‐O‐tert‐butyldiphenylsilyl‐2,3‐dideoxy‐D‐erythro‐furanoside (3) was coupled with silylated 5‐hydroxymethyluracil (1a) and its C1‐C6 alkyl ethers 1b–g to give the corresponding protected nucleosides 4a‐g which were deprotected with Bu4NF to afford 3‐azido nucleosides 5a‐g and 6a‐g. The α‐anomers 6f,g show moderate activity against HIV. No significant activity against HSV‐1 was found

  甲基3-叠氮基-5-O-叔丁基二苯基甲硅烷基-2,3-双脱氧-D-赤型-呋喃糖苷(3)与甲硅烷基化的5-羟甲基尿嘧啶(1a)及其C1-C6烷基醚1b-g偶联得到相应的受保护核苷 4a-g 用 Bu4NF 脱保护，得到 3-叠氮核苷 5a-g 和 6a-g。α-端基异构体 6f、g 对 HIV 表现出中等活性。未发现化合物 5 和 6 对 HSV-1 具有显着活性。