5-phenyl-2,4-bis(trimethylsilyloxy)pyrimidine | 159042-24-7

• 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-phenyl-2,4-bis(trimethylsilyloxy)pyrimidine
• CAS: 159042-24-7
• 化学式: C₁₆H₂₄N₂O₂Si₂
• 分子量: 332.55
• InChiKey: BZCXWUFBBNBIHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  44.24
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-phenyl-2,4-bis(trimethylsilyloxy)pyrimidine 在 palladium on activated charcoal 吡啶 、 1H-1,2,4-三唑 、 甲醇 、 ammonium hydroxide 、 硝酸乙酯 、 硫酸 、 氨 、 氢气 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 181.0h， 生成 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-(p-aminophenyl)cytosine
  参考文献：
  名称：

  Derivatives of 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-phenyluracil and 5-Benzyluracil. Synthesis and Biological Properties

  摘要：

  A number of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil and -cytosine nucleosides substituted at the 5 position with a nitrophenyl or nitrobenzyl group were synthesized from 5-phenyl- and 5-benzyluracil via condensation of the fluorinated sugar, followed by nitration. The corresponding amino analogues were also prepared by reduction of the nitro nucleosides. The uracil nucleosides were converted into the corresponding cytosine nucleosides by way of the triazole intermediates. None of these nucleosides exhibited significant activity against herpes simplex virus type 1 in Vero cells. However, cytosine nucleosides containing the o-nitrophenyl, p-nitrophenyl, p-nitrobenzyl or p-aminobenzyl substituent were found to be toxic (even at 1 mu M) to uninfected Vero cells, although they were essentially nontoxic in HL-60 cells. The 5'-monophosphates of the uracil nucleosides were inhibitors of the reaction catalyzed by purified Ehrlich ascites carcinoma thymidylate synthase, the 5-phenyluracil nucleotides causing a strong inhibition, competitive vs dUMP, described by the K-i value of 0.01 mu M.

  DOI：

  10.1080/15257779408013228
• 作为产物：
  描述：

  苯基丙二酸二乙酯 在 硫酸氢铵 作用下， 反应 2.0h， 生成 5-phenyl-2,4-bis(trimethylsilyloxy)pyrimidine
  参考文献：
  名称：

  Derivatives of 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-phenyluracil and 5-Benzyluracil. Synthesis and Biological Properties

  摘要：

  A number of 1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)uracil and -cytosine nucleosides substituted at the 5 position with a nitrophenyl or nitrobenzyl group were synthesized from 5-phenyl- and 5-benzyluracil via condensation of the fluorinated sugar, followed by nitration. The corresponding amino analogues were also prepared by reduction of the nitro nucleosides. The uracil nucleosides were converted into the corresponding cytosine nucleosides by way of the triazole intermediates. None of these nucleosides exhibited significant activity against herpes simplex virus type 1 in Vero cells. However, cytosine nucleosides containing the o-nitrophenyl, p-nitrophenyl, p-nitrobenzyl or p-aminobenzyl substituent were found to be toxic (even at 1 mu M) to uninfected Vero cells, although they were essentially nontoxic in HL-60 cells. The 5'-monophosphates of the uracil nucleosides were inhibitors of the reaction catalyzed by purified Ehrlich ascites carcinoma thymidylate synthase, the 5-phenyluracil nucleotides causing a strong inhibition, competitive vs dUMP, described by the K-i value of 0.01 mu M.

  DOI：

  10.1080/15257779408013228

文献信息

• Inhibitory Potency of 5-Benzyluracil, 5-Phenylcytosine and 5-Phenylpyrimidin-2-one Nucleosides Against Uridine Phosphorylase from Mouse Leukemic L1210 Cells
  作者：Ivan Votruba、Marcela Krečmerová、Hubert Hrˇebabecky´、Antonín Holý

  DOI：10.1080/07328319908044626

  日期：1999.11

  The inhibitory activity of a series of novel sugar-modified nucleosides derived from 5-benzyluracil, 5-phenylcytosine and 5-phenylpyrimidin-2-one against uridine phosphorylase purified from mouse leukemic L-1210 cells was investigated. Significant activity was encountered with O-2,O-2'-anhydro-5-benzylcytidine hydrochloride, 2',3'-dideoxy-5-benzyluridine, 2',3'-dideoxy-4-thiouridine and alpha- and beta-anomers of 5-benzyl-1-(2-deoxy-D-arabino-hexopyranosyl)uracil.