5'-deoxy-5'-fluoro-5-fluorouridine | 82207-49-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-deoxy-5'-fluoro-5-fluorouridine
• 英文别名: 5'-deoxy-5,5'-difluorouridine；5-fluoro-1-[(2R,3R,4S,5S)-5-(fluoromethyl)-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 82207-49-6
• 化学式: C₉H₁₀F₂N₂O₅
• 分子量: 264.186
• InChiKey: MVEGNDZJMMSVLR-UAKXSSHOSA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  99.1
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-氟-2',3'-异亚丙基尿苷 在 吡啶 、 potassium fluoride 、 三氟乙酸 作用下， 以 乙二醇 为溶剂， 反应 3.5h， 生成 5'-deoxy-5'-fluoro-5-fluorouridine
  参考文献：
  名称：

  Synthesis and biological activity of 5'-substituted 5-fluoropyrimidine nucleosides

  摘要：

  5'-Deoxy-5-fluorouridine (5'-dFUrd, 1) possesses a significantly higher chemotherapeutic index than other fluoropyrimidines as a result of its being selectivity cleaved in tumors to 5-fluorouracil (FUra) by uridine phosphorylase. Because 1 is a relatively poor substrate for this enzyme, we synthesized a series of 5'-deoxy-5'-substituted-5-fluorouridine (FUrd) derivatives in an effort to obtain compounds that might have improved substrate interactions compared to 1 and thus possibly be better prodrugs of FUra. Three derivatives, 5'-O-tosyl-FUrd (13), 5'-O-mesyl-FUrd (14), and 5'-deoxy-5'-bromo-FUrd (15), had cytostatic activity against L1210 and CCRF-CEM leukemic cells in culture superior to that of 1. In preliminary in vivo antitumor studies against L1210 leukemic cells in mice, 5'-deoxy-5'-chloro-FUrd (4), 5'-O-mesyl-FUrd (14), an 5'-deoxy-5'-fluoro-FUrd (18) gave percent increases in life span of 64, 58, and 58, respectively, compared to a value of 20 for compound 1.

  DOI：

  10.1021/jm00350a024

文献信息

• Fluorinase-Coupled Base Swaps: Synthesis of [¹⁸F]-5′-Deoxy-5′-fluorouridines
  作者：Margit Winkler、Juozas Domarkas、Lutz F. Schweiger、David O'Hagan

  DOI：10.1002/anie.200804040

  日期：2008.12.15
• Synthesis and biological activity of 5'-substituted 5-fluoropyrimidine nucleosides
  作者：Sudhir Ajmera、Peter V. Danenberg

  DOI：10.1021/jm00350a024

  日期：1982.8

  5'-Deoxy-5-fluorouridine (5'-dFUrd, 1) possesses a significantly higher chemotherapeutic index than other fluoropyrimidines as a result of its being selectivity cleaved in tumors to 5-fluorouracil (FUra) by uridine phosphorylase. Because 1 is a relatively poor substrate for this enzyme, we synthesized a series of 5'-deoxy-5'-substituted-5-fluorouridine (FUrd) derivatives in an effort to obtain compounds that might have improved substrate interactions compared to 1 and thus possibly be better prodrugs of FUra. Three derivatives, 5'-O-tosyl-FUrd (13), 5'-O-mesyl-FUrd (14), and 5'-deoxy-5'-bromo-FUrd (15), had cytostatic activity against L1210 and CCRF-CEM leukemic cells in culture superior to that of 1. In preliminary in vivo antitumor studies against L1210 leukemic cells in mice, 5'-deoxy-5'-chloro-FUrd (4), 5'-O-mesyl-FUrd (14), an 5'-deoxy-5'-fluoro-FUrd (18) gave percent increases in life span of 64, 58, and 58, respectively, compared to a value of 20 for compound 1.