3'-O-Acetyl-5-fluoro-2'-deoxyuridine-5'-monophosphate | 6216-72-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: 3'-O-Acetyl-5-fluoro-2'-deoxyuridine-5'-monophosphate
• 英文别名: O^3'-acetyl-5-fluoro-2'-deoxy-[5']uridylic acid；5-Fluor-3'-O-acetyl-2'-desoxy-uridin-5'-monophosphat；3'-O-Acetyl-2'-desoxy-5-fluor-uridylsaeure-(5')
• CAS: 6216-72-4
• 化学式: C₁₁H₁₄FN₂O₉P
• 分子量: 368.212
• InChiKey: FKVUPSZAPWHGJO-DJLDLDEBSA-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)：
  -1.0
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  157.15
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  氢化可的松 、 3'-O-Acetyl-5-fluoro-2'-deoxyuridine-5'-monophosphate 在 ammonium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 生成 5'-(Cortisol-21-phosphoryl)-5-fluoro-2'-deoxyuridine ammonium salt
  参考文献：
  名称：

  Nucleoside conjugates. 8. The preparation of 5-fluoro-2′-deoxyuridine conjugates of corticosteroids

  摘要：

  Three 5'-(steroid-21-phosphoryl)-5-fluoro-2'-deoxyuridines (VI-VIII) have been prepared and characterized by uv, ir, 1H-nmr, elemental analysis, chemical and enzymatic hydrolyses. These new compounds are 5-fluoro-2'-deoxyuridine conjugates of cortisol (VI), cortico-sterone (VII), and prednisolone (VIII). Besides the physical and analytical data, all of the conjugates were demonstrated to be enzymatically hydrolyzed to the corresponding steroid and 5-fluoro-2'-deoxyuridine 5'-monophosphate (III), and the latter was further shown to be hydrolyzed to 5-fluoro-2'-deoxyuridine (II) by phosphodiesterase I, 5'-nucleotidase, and acid phosphatase. However, they were shown to be resistant to hydrolysis by bacterial alkaline phosphatase.

  DOI：

  10.1016/0039-128x(86)90056-5
• 作为产物：
  描述：

  5'-O-trityl-3'-O-acetyl-5-fluoro-2'-deoxyuridine 在 ammonium hydroxide 、 水 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 3'-O-Acetyl-5-fluoro-2'-deoxyuridine-5'-monophosphate
  参考文献：
  名称：

  Nucleoside conjugates. 8. The preparation of 5-fluoro-2′-deoxyuridine conjugates of corticosteroids

  摘要：

  Three 5'-(steroid-21-phosphoryl)-5-fluoro-2'-deoxyuridines (VI-VIII) have been prepared and characterized by uv, ir, 1H-nmr, elemental analysis, chemical and enzymatic hydrolyses. These new compounds are 5-fluoro-2'-deoxyuridine conjugates of cortisol (VI), cortico-sterone (VII), and prednisolone (VIII). Besides the physical and analytical data, all of the conjugates were demonstrated to be enzymatically hydrolyzed to the corresponding steroid and 5-fluoro-2'-deoxyuridine 5'-monophosphate (III), and the latter was further shown to be hydrolyzed to 5-fluoro-2'-deoxyuridine (II) by phosphodiesterase I, 5'-nucleotidase, and acid phosphatase. However, they were shown to be resistant to hydrolysis by bacterial alkaline phosphatase.

  DOI：

  10.1016/0039-128x(86)90056-5