4-amino-8-(2,2-difluoro-2-deoxy-β-D-ribofuranosylamino)pyrimido<5,4-d>pyrimidine | 157130-58-0

• 分子结构分类: 有机化合物
• 英文名称: 4-amino-8-(2,2-difluoro-2-deoxy-β-D-ribofuranosylamino)pyrimido<5,4-d>pyrimidine
• 英文别名: (2R,3R,5R)-5-[(8-aminopyrimido[5,4-d]pyrimidin-4-yl)amino]-4,4-difluoro-2-(hydroxymethyl)oxolan-3-ol
• CAS: 157130-58-0
• 化学式: C₁₁H₁₂F₂N₆O₃
• 分子量: 314.251
• InChiKey: WWBTZSWVZRQFMN-XMRAEQSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  139
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-amino-8-(2,2-difluoro-2-deoxy-β-D-ribofuranosylamino)pyrimido<5,4-d>pyrimidine 反应 100.0h， 生成 4-amino-8-(2,2-difluoro-2-deoxy-β-D-ribopyranosylamino)pyrimido<5,4-d>pyrimidine 、 4-amino-8-(2,2-difluoro-2-deoxy-α-D-ribofuranosylamino)pyrimido<5,4-d>pyrimidine
  参考文献：
  名称：

  Synthesis of 4-Amino-8-(2, 2-Difluoro-2-Deoxy-β-D-Ribo Furanosyl Amino)Pyrimido [5, 4-D]Pyrimidine (dFARPP). Stability and Cellular Cytotoxicity

  摘要：

  The synthesis of beta-dFARPP was accomplished by Mitsunobu coupling of 6-cyanopurine with 2-deoxy-2,2-difluororibose followed by purine ring-expansion under the action of methanolic ammonia. The title compound inhibited the growth of proliferating human leukemic CCRF-CEM cells at 6.1 mu g/ml but had no effect on plaque formation by a variety of DNA and RNA viruses.

  DOI：

  10.1080/15257779408011883
• 作为产物：
  描述：

  9-(3,5-di-O-benzoyl-2,2-difluoro-2-deoxy-α/β-D-ribofuranosyl)purine-6-carbonitrile 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以15%的产率得到4-amino-8-(2,2-difluoro-2-deoxy-β-D-ribofuranosylamino)pyrimido<5,4-d>pyrimidine
  参考文献：
  名称：

  Synthesis of 4-Amino-8-(2, 2-Difluoro-2-Deoxy-β-D-Ribo Furanosyl Amino)Pyrimido [5, 4-D]Pyrimidine (dFARPP). Stability and Cellular Cytotoxicity

  摘要：

  The synthesis of beta-dFARPP was accomplished by Mitsunobu coupling of 6-cyanopurine with 2-deoxy-2,2-difluororibose followed by purine ring-expansion under the action of methanolic ammonia. The title compound inhibited the growth of proliferating human leukemic CCRF-CEM cells at 6.1 mu g/ml but had no effect on plaque formation by a variety of DNA and RNA viruses.

  DOI：

  10.1080/15257779408011883