diethyl 5-(2-amino-6-chloro-9H-purin-9-yl)-1,1-difluoro-3-methylpentylphosphonate | 876939-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: diethyl 5-(2-amino-6-chloro-9H-purin-9-yl)-1,1-difluoro-3-methylpentylphosphonate
• CAS: 876939-14-9
• 化学式: C₁₅H₂₃ClF₂N₅O₃P
• 分子量: 425.803
• InChiKey: HUZRDMSKTJGBQY-UHFFFAOYSA-N

物化性质

• 沸点：
  570.9±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  105.15
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  diethyl 5-(2-amino-6-chloro-9H-purin-9-yl)-1,1-difluoro-3-methylpentylphosphonate 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 生成 [5-(2-Amino-6-chloro-purin-9-yl)-1,1-difluoro-3-methyl-pentyl]-phosphonic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of 9-(5′,5′-difluoro-5′-phosphonopentyl)guanine derivatives for PNP-inhibitors

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)guanine (DFPP-G) and its hypoxanthine analogue (DFPP-H) were modified by introducing a methyl group to all possible positions of the linker connecting a purine and difluoromethylenephosphonic acid moiety to evaluate the effects of the methyl group on inhibition against purine nucleoside phosphorylase. The methyl group on the linker affected the inhibition in a positional-dependent manner. Inhibitory potency of alpha-methyl and beta-methyl -substituted analogues of DFPP-H increased by about 600- to 1000-fold upon converting to cyclopropane nucleotide analogue (+/-)-4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.017
• 作为产物：
  描述：

  4-diethoxyphosphoryl-5,5-difluoro-2-methylpentanoic acid 在 锂硼氢 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 24.0h， 生成 diethyl 5-(2-amino-6-chloro-9H-purin-9-yl)-1,1-difluoro-3-methylpentylphosphonate
  参考文献：
  名称：

  Synthesis and biological evaluation of 9-(5′,5′-difluoro-5′-phosphonopentyl)guanine derivatives for PNP-inhibitors

  摘要：

  9-(5',5'-Difluoro-5'-phosphonopentyl)guanine (DFPP-G) and its hypoxanthine analogue (DFPP-H) were modified by introducing a methyl group to all possible positions of the linker connecting a purine and difluoromethylenephosphonic acid moiety to evaluate the effects of the methyl group on inhibition against purine nucleoside phosphorylase. The methyl group on the linker affected the inhibition in a positional-dependent manner. Inhibitory potency of alpha-methyl and beta-methyl -substituted analogues of DFPP-H increased by about 600- to 1000-fold upon converting to cyclopropane nucleotide analogue (+/-)-4. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.10.017