9-(6'-deoxy-β-D-allofuranosyl)-6-thiopurine | 2946-43-2

• 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: 9-(6'-deoxy-β-D-allofuranosyl)-6-thiopurine
• 英文别名: 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(1-hydroxyethyl)oxolan-2-yl]-3H-purine-6-thione
• CAS: 2946-43-2
• 化学式: C₁₁H₁₄N₄O₄S
• 分子量: 298.323
• InChiKey: LMTPULIBTJWSQT-ONBHVAQOSA-N

物化性质

• 沸点：
  690.0±65.0 °C(Predicted)
• 密度：
  1.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-chloro-9-trimethylsilylpurine 在 氨 、 氰化汞 、 硫脲 、 mercury dibromide 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 124.0h， 生成 9-(6'-deoxy-β-D-allofuranosyl)-6-thiopurine
  参考文献：
  名称：

  Synthesis of hypoxanthine, guanine, and 6-thiopurine nucleosides of 6-deoxy-D-allofuranose

  摘要：

  Hypoxanthine, guanine, and 6-thiopurine nucleosides of 6-deoxy-D-allofuranose have been prepared as potential antitumor agents. Thus, reaction of 6-deoxy-beta-D-allofuranosyl bromide (1) with the trimethylsilyl derivatives of hypoxanthine and guanine afforded mixtures of the 9- and the 7-substituted bases, which were separated and deblocked with ammonia to give 9-(6'-deoxy-beta-D-allofuranosyl)hypoxanthine (6), 7-(6'-deoxy-beta-D-allofuranosyl)hypoxanthine (7), 9-(6'-deoxy-beta-D-allofuranosyl)guanine (8), and 7-(6'-deoxy-beta-D-allofuranosyl)guanine (9). The two nucleosides with the purine joined at the N-9 position, namely, 6 and 8, are easily distinguished from the other two nucleosides (7 and 9), having N-7 junctions, by their NMR spectra. Reaction of 1 with the trimethylsilyl derivative of 6-chloropurine afforded 10, which upon treatment with thiourea and deblocking gave 9-(6'-deoxy-beta-D-allofuranosyl)-6-thiopurine (12). The hypoxanthine and guanine nucleosides showed no inhibition of mouse leukemia L1210 when tested in vivo, but the thiopurine nucleoside 12 showed strong inhibition of growth of L1210 both in vivo and in vitro. Compound 7 strongly inhibited purine nucleoside phosphorylase (KI = 8.8 X 10(-5) M), while compounds 8, 9, 6, and 12 were inactive.

  DOI：

  10.1021/jm00361a023