N(4)-丁二酰-1-beta-D-阿拉伯呋喃糖基胞嘧啶 | 55726-37-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 中文名称: N(4)-丁二酰-1-beta-D-阿拉伯呋喃糖基胞嘧啶
• 英文名称: cytarabine-succinic acid monoester
• 英文别名: 4-(1-β-D-arabinofuranosyl-2-oxo-1,2-dihydro-pyrimidin-4-ylamino)-4-oxo-butyric acid；N(4)-Succinyl-1-beta-D-arabinofuranosylcytosine；4-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-4-oxobutanoic acid
• CAS: 55726-37-9
• 化学式: C₁₃H₁₇N₃O₈
• 分子量: 343.293
• InChiKey: GFDPKOGBJRXYAE-IJJXPJNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  169
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (5-fluoro-2,4-dioxopyrimidin-1-yl)methyl 4-[[1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]amino]-4-oxobutanoate 在 potassium dihydrogen phosphate buffer 作用下， 生成 聚合甲醛 、 5-氟脲嘧啶 、 N(4)-丁二酰-1-beta-D-阿拉伯呋喃糖基胞嘧啶
  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

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.