5'-deoxy-5'-<(phenoxycarbonyl)amino>inosine | 76563-06-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 5'-deoxy-5'-<(phenoxycarbonyl)amino>inosine
• 英文别名: 5'-deoxy-5'-[(phenoxycarbonyl)amino]inosine
• CAS: 76563-06-9
• 化学式: C₁₇H₁₇N₅O₆
• 分子量: 387.352
• InChiKey: DWWPQAILIQGENW-XNIJJKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.47
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  151.59
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  5'-Amino-5'-desoxyinosin 、 氯甲酸苯酯 在 三乙胺 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 1.0h， 以75%的产率得到5'-deoxy-5'-<(phenoxycarbonyl)amino>inosine
  参考文献：
  名称：

  Nucleosides containing chemically reactive groups

  摘要：

  5'-Amino-5'-deoxyinosine (1) and 1-(6-amino-2,5,6-trideoxy-beta-D-erythro-hexofuranosyl)thymine (9) were prepared and substituted on the amino group with chemically reactive functions in an effort to find inhibitors of enzymes that metabolize the corresponding nucleotides. The resulting 5'-substituted methynitrosoureas 3, 11a, and 11b, bromoacetamides 4 and 13, phenyl carbamates 5 and 14, and 4-(fluorosulfonyl)benzamides 6 and 15 were tested for cytotoxicity to H.Ep-2 cells in culture and as inhibitors of incorporation of precursors into nucleic acids of L1210 cells. The inosine derivatives were also evaluated as inhibitors of hypoxanthine phosphoribosyltransferase. Compounds 4, 6 and 13 showed moderate inhibition of formation of nucleic acids, and compound 4 demonstrated significant cytotoxicity (ED50 less than 5 microgram/mL).

  DOI：

  10.1021/jm00135a021