6-(methylthio)-9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine | 76265-49-1

• 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: 6-(methylthio)-9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine
• 英文别名: 6-(methylthio)-9-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)purine
• CAS: 76265-49-1
• 化学式: C₁₇H₂₀N₄O₇S
• 分子量: 424.434
• InChiKey: HTLGKOCQNIEPKQ-MBMVNNNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.87
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  131.73
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  6-(methylthio)-9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine 在 potassium permanganate 、 氨 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 4-amino-8-(β-D-arabinofuranosylamino)pyrimido<5,4-d>pyrimidine
  参考文献：
  名称：

  Synthesis and biological evaluation of certain 2'-deoxy-.beta.-D-ribo-and 2.beta.-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine

  摘要：

  The key intermediate 9-(2,3,5,-tri-O-acetyl-beta-D-arabinofuranosyl)purine-6-carbonitrile (7) was synthesized in four steps from 9-beta-D-arabinofuranosylpurine-6-thione (3) via 6-(methylsulfonyl)-9-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)purine (6). Reaction of compound 7 with methanolic ammonia provided the rearranged compound 4-amino-8-(beta-D-arabinofuranosylamino)pyrimido[5,4-d]pyrimidine (8). Treatment of 7 with ammonium hydroxide and hydrogen peroxide provided 9-beta-D-arabinofuranosylpurine-6-carboxamide (9). Compound 7 was also treated with sodium hydrosulfide to yield 9-beta-D-arabinofuranosylpurine-6-thiocarboxamide (10). Similarly, 9-(2-deoxy-3,5-di-O-acetyl-beta-D-erythro-pentofuranosyl)purine 6-carbonitrile (17) was prepared from 6-chloro-9-(2-deoxy-beta-D-erythro-pentofluranosyl)purine (11) via 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-thione. Compound 17 was converted into 4-amino-8-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]pyrimido[5,4-d]pyrimidi ne (18) and 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-carboxamide (20), respectively. Compound 2 showed immunosuppressive activity and also inhibited the growth of L-1210 leukemia in mice. Arabinonucleoside analogues 8-10 were inactive when tested against RNA and DNA viruses in cell culture.

  DOI：

  10.1021/jm00136a008
• 作为产物：
  描述：

  6-巯基嘌呤阿拉伯糖苷 在 4-二甲氨基吡啶 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 6-(methylthio)-9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine
  参考文献：
  名称：

  Synthesis and biological evaluation of certain 2'-deoxy-.beta.-D-ribo-and 2.beta.-D-arabinofuranosyl nucleosides of purine-6-carboxamide and 4,8-diaminopyrimido[5,4-d]pyrimidine

  摘要：

  The key intermediate 9-(2,3,5,-tri-O-acetyl-beta-D-arabinofuranosyl)purine-6-carbonitrile (7) was synthesized in four steps from 9-beta-D-arabinofuranosylpurine-6-thione (3) via 6-(methylsulfonyl)-9-(2,3,5-tri-O-acetyl-beta-D-arabinofuranosyl)purine (6). Reaction of compound 7 with methanolic ammonia provided the rearranged compound 4-amino-8-(beta-D-arabinofuranosylamino)pyrimido[5,4-d]pyrimidine (8). Treatment of 7 with ammonium hydroxide and hydrogen peroxide provided 9-beta-D-arabinofuranosylpurine-6-carboxamide (9). Compound 7 was also treated with sodium hydrosulfide to yield 9-beta-D-arabinofuranosylpurine-6-thiocarboxamide (10). Similarly, 9-(2-deoxy-3,5-di-O-acetyl-beta-D-erythro-pentofuranosyl)purine 6-carbonitrile (17) was prepared from 6-chloro-9-(2-deoxy-beta-D-erythro-pentofluranosyl)purine (11) via 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-thione. Compound 17 was converted into 4-amino-8-[(2-deoxy-beta-D-erythro-pentofuranosyl)amino]pyrimido[5,4-d]pyrimidi ne (18) and 9-(2-deoxy-beta-D-erythro-pentofuranosyl)purine-6-carboxamide (20), respectively. Compound 2 showed immunosuppressive activity and also inhibited the growth of L-1210 leukemia in mice. Arabinonucleoside analogues 8-10 were inactive when tested against RNA and DNA viruses in cell culture.

  DOI：

  10.1021/jm00136a008