2,7-diamino-1-hydroxymitosene 1-(5-fluoro-2'-deoxyuridylate)

• 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: 2,7-diamino-1-hydroxymitosene 1-(5-fluoro-2'-deoxyuridylate)
• 英文别名: [2,6-diamino-3-[[(2R,3S,5R)-5-(5-fluoro-2,4-dioxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-7-methyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-4-yl]methyl carbamate
• 化学式: C₂₃H₂₆FN₆O₁₂P
• 分子量: 628.465
• InChiKey: TVCQEOHNUNACPT-BRBIXOKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  278
• 氢给体数：
  6
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  丝裂霉素 C 、 sodium 5-fluoro-2'-deoxyuridylate 在 高氯酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以30%的产率得到2,7-diamino-1-hydroxymitosene 1-(5-fluoro-2'-deoxyuridylate)
  参考文献：
  名称：

  Nucleotide derivatives of 2,7-diaminomitosene

  摘要：

  Treatment of mitomycin C with pyrimidine nucleotides in acidic media produced derivatives of 2,7-diaminomitosene in which C-1 was covalently bound to the phosphate group of the nucleotides. On reduction, these derivatives liberated the nucleotides and a mitomycin intermediate that alkylated DNA. Their reduction in the presence of 2'-deoxyguanosine produced some bifunctional alkylation as did mitomycin C. They were readily taken up by L1210 leukemia cells, in which they showed potent cytotoxicity. These properties suggest that they are acting as prodrugs capable of conversion into two active species. The uridylate derivative showed activity comparable to that of mitomycin C against P-388 leukemia in mice.

  DOI：

  10.1021/jm00403a016

文献信息

• Nucleotide derivatives of 2,7-diaminomitosene
  作者：Bhashyam S. Iyengar、Robert T. Dorr、William A. Remers、Charles D. Kowal

  DOI：10.1021/jm00403a016

  日期：1988.8

  Treatment of mitomycin C with pyrimidine nucleotides in acidic media produced derivatives of 2,7-diaminomitosene in which C-1 was covalently bound to the phosphate group of the nucleotides. On reduction, these derivatives liberated the nucleotides and a mitomycin intermediate that alkylated DNA. Their reduction in the presence of 2'-deoxyguanosine produced some bifunctional alkylation as did mitomycin C. They were readily taken up by L1210 leukemia cells, in which they showed potent cytotoxicity. These properties suggest that they are acting as prodrugs capable of conversion into two active species. The uridylate derivative showed activity comparable to that of mitomycin C against P-388 leukemia in mice.