(1'RS)-5-Fluoro-1-(1'-methoxy-2'-methoxycarbonylethyl)uracil | 133625-57-7

• 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: (1'RS)-5-Fluoro-1-(1'-methoxy-2'-methoxycarbonylethyl)uracil
• 英文别名: Methyl 3-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-methoxypropanoate
• CAS: 133625-57-7
• 化学式: C₉H₁₁FN₂O₅
• 分子量: 246.195
• InChiKey: QGZOSDSKUDABFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 3，3-二甲氧基丙酸甲酯 在 三甲基氯硅烷 、 四氯化锡 、 六甲基二硅氮烷 作用下， 以 乙腈 为溶剂， 以45.3%的产率得到(1'RS)-5-Fluoro-1-(1'-methoxy-2'-methoxycarbonylethyl)uracil
  参考文献：
  名称：

  Synthesis and evaluation of new 5-fluorouracil antitumor cell differentiating derivatives

  摘要：

  Three new antitumour drugs containing two 5-fluorouracil moieties at both ends of the structure and a two amide bond linker were synthesized. Appropriated bis-acetal were reacted with two equivalents of 5-FU to afford the desired compounds. These drugs were evaluated for their ability to induce myogenic maturation in vitro on human rhabdomyosarcoma cells in an experimental model. Compounds 5 and 6 induced morphological and phenotypical differentiation in rhabdomyosarcoma cells at 4.5 and 3.5 muM, respectively. These new cell differentiating agents could be used as an alternative to selective destruction Of undifferentiated cells. A potential role of the differentiation therapy as an alternative approach to the treatment of rhabdomyosarcomas is suggested. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00464-9

文献信息

• Tietze, Lutz F.; Krach, Thomas; Beller, Matthias, Chemische Berichte, 1991, vol. 124, # 9, p. 2019 - 2024
  作者：Tietze, Lutz F.、Krach, Thomas、Beller, Matthias、Arlt, Michael

  DOI：——

  日期：——
• Synthesis and evaluation of new 5-fluorouracil antitumor cell differentiating derivatives
  作者：José F. Domı́nguez、Juan A. Marchal、Antonio Correa、Esmeralda Carrillo、Houria Boulaiz、Antonia Aránega、Miguel A. Gallo、Antonio Espinosa

  DOI：10.1016/s0968-0896(02)00464-9

  日期：2003.2

  Three new antitumour drugs containing two 5-fluorouracil moieties at both ends of the structure and a two amide bond linker were synthesized. Appropriated bis-acetal were reacted with two equivalents of 5-FU to afford the desired compounds. These drugs were evaluated for their ability to induce myogenic maturation in vitro on human rhabdomyosarcoma cells in an experimental model. Compounds 5 and 6 induced morphological and phenotypical differentiation in rhabdomyosarcoma cells at 4.5 and 3.5 muM, respectively. These new cell differentiating agents could be used as an alternative to selective destruction Of undifferentiated cells. A potential role of the differentiation therapy as an alternative approach to the treatment of rhabdomyosarcomas is suggested. (C) 2002 Elsevier Science Ltd. All rights reserved.