5'-deoxy-5'-amino-5-fluorouridine | 82207-47-4

• 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'-amino-5-fluorouridine
• 英文别名: 5'-amino-5'-deoxy-5-fluorouridine；5'-Amino-5'-deoxy-5-fluorouridine；1-[(2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]-5-fluoropyrimidine-2,4-dione
• CAS: 82207-47-4
• 化学式: C₉H₁₂FN₃O₅
• 分子量: 261.21
• InChiKey: CFRPQDDBSNZLHF-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)：
  -1.9
• 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：
  125
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5'-deoxy-5'-amino-5-fluorouridine 、 方酸二乙酯 在 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 以11.7 mg的产率得到1-((2R,3R,4S,5R)-5-(((2-ethoxy-3,4-dioxocyclobut-1-en-1-yl)amino)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-fluoropyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Squaryl group-modified UDP analogs as inhibitors of the endoplasmic reticulum-resident folding sensor enzyme UGGT

  摘要：

  UDP-Glc：糖蛋白葡萄糖基转移酶（UGGT）在内质网（ER）中具有中心作用，以保持正确折叠的N-糖基蛋白的质量控制。

  DOI：

  10.1039/d2cc06634c
• 作为产物：
  描述：

  5-氟-2',3'-异亚丙基尿苷 在 吡啶 、 叠氮化锂 、 三苯基膦 、 三氟乙酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 5'-deoxy-5'-amino-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

• Synthesis and in vivo antitumor activity of potential 5-fluorouracil prodrugs
  作者：A. Rosowsky、S. H. Kim、D. Trites、M. Wick

  DOI：10.1021/jm00351a006

  日期：1982.9
• 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.
• Squaryl group-modified UDP analogs as inhibitors of the endoplasmic reticulum-resident folding sensor enzyme UGGT
  作者：Junpei Abe、Yoichi Takeda、Takashi Kikuma、Yasuhiko Kizuka、Hiroyuki Kajiura、Yasuhiro Kajihara、Yukishige Ito

  DOI：10.1039/d2cc06634c

  日期：——

  UDP-Glc:glycoprotein glucosyltransferase (UGGT) has a central role to retain quality control of correctly folded N-glycoprotein in the endoplasmic reticulum (ER).

  UDP-Glc：糖蛋白葡萄糖基转移酶（UGGT）在内质网（ER）中具有中心作用，以保持正确折叠的N-糖基蛋白的质量控制。