5-benzyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil | 159042-30-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-benzyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil
• 英文别名: 5-benzyl-1-[(2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 159042-30-5
• 化学式: C₁₆H₁₇FN₂O₅
• 分子量: 336.32
• InChiKey: IFIWQIWRYUFUJN-QVHKTLOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-benzyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 在 磷酸三乙酯 、 三氯氧磷 作用下， 反应 8.0h， 生成 5-benzyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil 5'-monophosphate
  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：

  5-苄基巴比妥酸 在 吡啶 、 甲醇 、 硫酸氢铵 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 194.0h， 生成 5-benzyl-1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)uracil
  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

• Derivatives of 1-(2-Deoxy-2-fluoro-β-D-arabinofuranosyl)-5-phenyluracil and 5-Benzyluracil. Synthesis and Biological Properties
  作者：Krzysztof Dziewiszek、Raymond F. Schinazi、Ting-Chao Chou、Tsann-Long Su、Jolanta M. Dzik、Wojciech Rode、Kyoichi A. Watanabe

  DOI：10.1080/15257779408013228

  日期：1994.3

  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.