2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine | 156357-14-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine
• CAS: 156357-14-1
• 化学式: C₂₄H₂₁FN₆O₅
• 分子量: 492.466
• InChiKey: QYLRVXDEMDFASO-BZSOYRFXSA-N

物化性质

• 沸点：
  767.9±70.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  36.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  157.47
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到2-氨基-2'-氟-2'-脱氧腺苷
  参考文献：
  名称：

  Synthesis and Biologic Activity of Purine 2′-Deoxy-2′-fluoro-ribonucleosides

  摘要：

  The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

  DOI：

  10.1080/15257779408013243
• 作为产物：
  描述：

  2,6-二氯嘌呤 在 palladium on activated charcoal sodium azide 、 氢气 、 氰化汞 作用下， 以 乙醇 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 65.0h， 生成 2,6-diamino-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-β-D-ribofuranosyl)purine
  参考文献：
  名称：

  Synthesis and Biologic Activity of Purine 2′-Deoxy-2′-fluoro-ribonucleosides

  摘要：

  The synthesis of 3,5-di-O-benzoyl-2-deoxy-2-fluoro-D-ribofuranosyl bromide (8) and its reaction with 2,6-dichloropurine by fusion and with mercuric cyanide catalysis is described. The resulting 2,6-dichloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-ribofuranosyl)purine (13) was converted to the 2-fluoroadenine (16), the 2-chloroadenine (17), 2,6-diaminopurine (12), and guanine (14) nucleosides by standard procedures. These nucleosides were cytotoxic to a number of cell lines in culture. The 2-haloadenine nucleosides 16 and 17 gave modest increases in lifespan when tested against the P388 leukemia in mice.

  DOI：

  10.1080/15257779408013243