(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 6-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-6-oxohexanoate | 201210-77-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 6-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-6-oxohexanoate
• CAS: 201210-77-7
• 化学式: C₂₀H₂₄FN₅O₁₀
• 分子量: 513.436
• InChiKey: DLJRAKXAGIQNEP-NEDOFYQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  207
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 6-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-6-oxohexanoate 在 碳酸氢钠 、 sodium carbonate 作用下， 生成 聚合甲醛 、 5-氟脲嘧啶 、
  参考文献：
  名称：

  Synthesis and Reactivity of 5-Fluorouracil/Cytarabine Mutual Prodrugs

  摘要：

  Two mutual prodrugs, in which two different anti-cancer drugs are attached to the same molecule via labile linkages, are synthesized and examined kinetically. One of the mutual prodrugs loses a drug component under physiological conditions within an hour, but the other mutual prodrug (having a longer spacer between the two drugs) is stable to chemical degradation even at higher pH values. Thus, enzymatic hydrolysis alone will release the two anti-cancer drugs. The potential value of anti-cancer mutual prodrugs is discussed.

  DOI：

  10.1021/jo971076p
• 作为产物：
  描述：

  6-[(5-Fluoro-2,4-dioxopyrimidin-1-yl)methoxy]-6-oxohexanoic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 98.0h， 生成 (5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 6-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-6-oxohexanoate
  参考文献：
  名称：

  Synthesis and Reactivity of 5-Fluorouracil/Cytarabine Mutual Prodrugs

  摘要：

  Two mutual prodrugs, in which two different anti-cancer drugs are attached to the same molecule via labile linkages, are synthesized and examined kinetically. One of the mutual prodrugs loses a drug component under physiological conditions within an hour, but the other mutual prodrug (having a longer spacer between the two drugs) is stable to chemical degradation even at higher pH values. Thus, enzymatic hydrolysis alone will release the two anti-cancer drugs. The potential value of anti-cancer mutual prodrugs is discussed.

  DOI：

  10.1021/jo971076p

文献信息

• Synthesis and Reactivity of 5-Fluorouracil/Cytarabine Mutual Prodrugs
  作者：Fredric M. Menger、Michael J. Rourk

  DOI：10.1021/jo971076p

  日期：1997.12.1

  Two mutual prodrugs, in which two different anti-cancer drugs are attached to the same molecule via labile linkages, are synthesized and examined kinetically. One of the mutual prodrugs loses a drug component under physiological conditions within an hour, but the other mutual prodrug (having a longer spacer between the two drugs) is stable to chemical degradation even at higher pH values. Thus, enzymatic hydrolysis alone will release the two anti-cancer drugs. The potential value of anti-cancer mutual prodrugs is discussed.