9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile | 76265-54-8

• 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-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile
• CAS: 76265-54-8
• 化学式: C₁₅H₁₅N₅O₅
• 分子量: 345.315
• InChiKey: QBRAREWREPGATO-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.48
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129.22
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile 在 ammonium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 21.0h， 以46%的产率得到9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carboxamide
  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：

  ((2R,3S,5R)-3-乙酰氧基-5-(6-(甲硫基)-9H-嘌呤-9-基)四氢呋喃-2-基)乙酸甲酯 在 间氯过氧苯甲酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 9-(2-deoxy-3,5-di-O-acetyl-β-D-erythro-pentofuranosyl)purine-6-carbonitrile
  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