6-(methylthio)-9-β-D-arabinofuranosylpurine | 13153-62-3

• 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-β-D-arabinofuranosylpurine
• 英文别名: 6-(methylmercapto)-9-(β-D-arabinofuranosyl)-9H-purine；9-(β-D-Arabinofuranosyl)-6-methylthio-9H-purin；1-(6-methylsulfanyl-purin-9-yl)-β-D-1-deoxy-arabinofuranose；(2R,3S,4S,5R)-2-(Hydroxymethyl)-5-(6-(methylthio)-9H-purin-9-yl)tetrahydrofuran-3,4-diol；(2R,3S,4S,5R)-2-(hydroxymethyl)-5-(6-methylsulfanylpurin-9-yl)oxolane-3,4-diol
• CAS: 13153-62-3
• 化学式: C₁₁H₁₄N₄O₄S
• 分子量: 298.323
• InChiKey: ZDRFDHHANOYUTE-ICQCTTRCSA-N

物化性质

• 沸点：
  636.3±65.0 °C(Predicted)
• 密度：
  1.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-(methylthio)-9-β-D-arabinofuranosylpurine 在 4-二甲氨基吡啶 、 potassium permanganate 作用下， 以 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 9-(2,3,5-tri-O-acetyl-β-D-arabinofuranosyl)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
• 作为产物：
  描述：

  6-巯基嘌呤阿拉伯糖苷 、 碘甲烷 以 potassium carbonate 、 二甲基亚砜 为溶剂， 生成 6-(methylthio)-9-β-D-arabinofuranosylpurine
  参考文献：
  名称：

  Purine sugar derivatives

  摘要：

  本发明涉及嘌呤糖衍生物，其作为免疫反应抑制剂和抗病毒剂有用，并涉及其制备方法。

  公开号：

  US03956277A1

文献信息

• Purine sugar derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US03956277A1

  公开（公告）日：1976-05-11

  This invention relates to purine sugar derivatives which are useful as suppressors of the immune response and as antiviral agents, and to methods of preparation thereof.

  本发明涉及嘌呤糖衍生物，其作为免疫反应抑制剂和抗病毒剂有用，并涉及其制备方法。
• 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
  作者：Prem C. Srivastava、Ganapathi R. Revankar、Roland K. Robins、Robert J. Rousseau

  DOI：10.1021/jm00136a008

  日期：1981.4

  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.