N1-(2-furanidyl)-N3-(2-hydroxethyl)-5-fluorouracil | 290815-84-8

• 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: N1-(2-furanidyl)-N3-(2-hydroxethyl)-5-fluorouracil
• 英文别名: N¹-(2-furanidyl)-N³-(2-hydroxethyl)-5-fluorouracil
• CAS: 290815-84-8
• 化学式: C₁₀H₁₃FN₂O₄
• 分子量: 244.223
• InChiKey: MMZQCAHRYVWFCI-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.55
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  73.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N1-(2-furanidyl)-N3-(2-hydroxethyl)-5-fluorouracil 在 碘 、 sulfur 、 六乙基亚磷酸胺 作用下， 以 苯 为溶剂， 反应 4.5h， 生成 (2S,4S)-2-[2-((S)-5-Fluoro-2,6-dioxo-3-tetrahydro-furan-2-yl-3,6-dihydro-2H-pyrimidin-1-yl)-ethoxy]-2-thioxo-2λ⁵-[1,3,2]oxazaphospholidine-4-carboxylic acid octyl ester
  参考文献：
  名称：

  SYNTHESIS OF NOVEL OPTICALLY ACTIVE CYCLIC PHOSPHOLIPID CONJUGATES OF TEGAFUR AND URIDINE STARTING FROM L-SERINE

  摘要：

  Starting from L-serine, cyclic thiophosphoramidate conjugates (2 and 3) of Tegafur and uridine were synthesized via a multiple-step procedure of esterification, cyclic phosphorylation, and sulfurization, etc. L-serinoate was N-alkylated, then cyclized with phosphorus oxychloride, and further reacted with N-3-(2-hydroxyethyl) Tegafur to afford cyclic phospholipid conjugate 4. The resultants (2, 3, and 4) were successfully separated in the form of pure diastereomer by column chromatography on silica gel. Their configurations were discussed and assigned according to their NMR spectra. The asymmetric induction effects of the carbon-based chiral centre on the diastereomer preference were also observed in these two synthetic phosphorylation cyclizations. The bioassay on their antitumor activities is under investigation.

  DOI：

  10.1080/10426500008043682
• 作为产物：
  描述：

  (S)-替加氟 、 2-溴乙醇 在 三乙胺 作用下， 以 乙腈 为溶剂， 以78%的产率得到N1-(2-furanidyl)-N3-(2-hydroxethyl)-5-fluorouracil
  参考文献：
  名称：

  SYNTHESIS OF NOVEL OPTICALLY ACTIVE CYCLIC PHOSPHOLIPID CONJUGATES OF TEGAFUR AND URIDINE STARTING FROM L-SERINE

  摘要：

  Starting from L-serine, cyclic thiophosphoramidate conjugates (2 and 3) of Tegafur and uridine were synthesized via a multiple-step procedure of esterification, cyclic phosphorylation, and sulfurization, etc. L-serinoate was N-alkylated, then cyclized with phosphorus oxychloride, and further reacted with N-3-(2-hydroxyethyl) Tegafur to afford cyclic phospholipid conjugate 4. The resultants (2, 3, and 4) were successfully separated in the form of pure diastereomer by column chromatography on silica gel. Their configurations were discussed and assigned according to their NMR spectra. The asymmetric induction effects of the carbon-based chiral centre on the diastereomer preference were also observed in these two synthetic phosphorylation cyclizations. The bioassay on their antitumor activities is under investigation.

  DOI：

  10.1080/10426500008043682