9-[8',8'-difluoro-8'-(diethylphosphono)oct-1'-ynyl]-2-N-(N,N-dimethylaminomethylidene)-1N-(pivaloyloxy)methyl-9-deazaguanine | 1225194-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 9-[8',8'-difluoro-8'-(diethylphosphono)oct-1'-ynyl]-2-N-(N,N-dimethylaminomethylidene)-1N-(pivaloyloxy)methyl-9-deazaguanine
• CAS: 1225194-34-2
• 化学式: C₂₇H₄₀F₂N₅O₆P
• 分子量: 599.615
• InChiKey: SUPWVGUYVSSMIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  41.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  128.11
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  9-[8',8'-difluoro-8'-(diethylphosphono)oct-1'-ynyl]-2-N-(N,N-dimethylaminomethylidene)-1N-(pivaloyloxy)methyl-9-deazaguanine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 0.33h， 以84%的产率得到9-[8',8'-difluoro-8'-(diethylphosphono)octyl]-2-N-(N,N-dimethylaminomethylidene)-1N-(pivaloyloxy)methyl-9-deazaguanine
  参考文献：
  名称：

  Structural-based design and synthesis of novel 9-deazaguanine derivatives having a phosphate mimic as multi-substrate analogue inhibitors for mammalian PNPs

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)-9-deazaguanine (DFPP-DG) was designed as a multi-substrate analogue inhibitor against purine nucleoside phosphorylase (PNP) on the basis of X-ray crystallographic data obtained for a binary complex of 9-(5',5'-difluoro-5'-phosphonopentyl)guanine (DFPP-G) with calf-spleen PNP. DFPP-DG and its analogous compounds were synthesized by the Sonogashira coupling reaction between a 9-deaza-9-iodoguanine derivative and omega-alkynyldifluoromethylene phosphonates as a key reaction. The experimental details focused on the synthetic chemistry along with some insights into the physical and biological properties of newly synthesized DFPP-DG derivatives are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.062
• 作为产物：
  描述：

  9-[8',8'-difluoro-8'-(diethylphosphono)oct-1'-ynyl]-2-N-(N,N-dimethylaminomethylidene)-7-N-(2-nitrophenyl)sulfonyl-1N-(pivaloyloxy)methyl-9-deazaguanine 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以100%的产率得到9-[8',8'-difluoro-8'-(diethylphosphono)oct-1'-ynyl]-2-N-(N,N-dimethylaminomethylidene)-1N-(pivaloyloxy)methyl-9-deazaguanine
  参考文献：
  名称：

  Structural-based design and synthesis of novel 9-deazaguanine derivatives having a phosphate mimic as multi-substrate analogue inhibitors for mammalian PNPs

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)-9-deazaguanine (DFPP-DG) was designed as a multi-substrate analogue inhibitor against purine nucleoside phosphorylase (PNP) on the basis of X-ray crystallographic data obtained for a binary complex of 9-(5',5'-difluoro-5'-phosphonopentyl)guanine (DFPP-G) with calf-spleen PNP. DFPP-DG and its analogous compounds were synthesized by the Sonogashira coupling reaction between a 9-deaza-9-iodoguanine derivative and omega-alkynyldifluoromethylene phosphonates as a key reaction. The experimental details focused on the synthetic chemistry along with some insights into the physical and biological properties of newly synthesized DFPP-DG derivatives are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.062