1-O-[(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl] 6-O-(2,3,4,5,6-pentafluorophenyl) hexanedioate | 201210-75-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 1-O-[(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl] 6-O-(2,3,4,5,6-pentafluorophenyl) hexanedioate
• CAS: 201210-75-5
• 化学式: C₁₇H₁₂F₆N₂O₆
• 分子量: 454.282
• InChiKey: LAXYELUBIVBINC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-O-[(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl] 6-O-(2,3,4,5,6-pentafluorophenyl) hexanedioate 、 阿糖胞苷 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以66%的产率得到(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
• 作为产物：
  描述：

  1-O-benzyl 6-O-(phenylsulfanylmethyl) hexanedioate 在 palladium on activated charcoal 磺酰氯 、 1,4-环己二烯 、 cis-1,2,3,6-tetrahydrophthalic acid 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 1-O-[(5-fluoro-2,4-dioxopyrimidin-1-yl)methyl] 6-O-(2,3,4,5,6-pentafluorophenyl) hexanedioate
  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.