(3S,4S)-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethylpyrrolidin-3-ol | 1058142-13-4

• 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: (3S,4S)-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethylpyrrolidin-3-ol
• 英文别名: F-DADMe-ImmH；Immucillins, 1；7-[[(3S,4S)-3-fluoro-4-hydroxy-3-(hydroxymethyl)pyrrolidin-1-yl]methyl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
• CAS: 1058142-13-4
• 化学式: C₁₂H₁₅FN₄O₃
• 分子量: 282.275
• InChiKey: VFUSATHXTREUCA-UFBFGSQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  101
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 (3S,4S)-4-fluoro-4-(hydroxymethyl)pyrrolidin-3-ol 、 1,5-二氢-4H-吡咯并[3,2-D]嘧啶-4-酮 在 sodium acetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 (3S,4S)-1-((9-deazahypoxanthin-9-yl)methyl)-4-fluoro-4-hydroxymethylpyrrolidin-3-ol
  参考文献：
  名称：

  A β-Fluoroamine Inhibitor of Purine Nucleoside Phosphorylase

  摘要：

  The potent immucillin purine nucleoside phosphorylase (PNP) inhibitors F-DADMe-ImmH [(3S,4S)-3], and [(3R,4R)-3] are synthesized in seven steps. Cycloaddition to a fluoroalkene and an enzymic resolution are the key features of the construction of the fluoropyrrolidines 11, from which the immucillins are assembled by use of a three-component Mannich reaction. Slow-onset binding constants (K(i)*) for [(3S,4S)-3] and [(3R,4R)-3] with human PNP are 0.032 and 1.82 nM, respectively. F-DADMe-ImmH [(3S,4S)-3] exhibits oral availability in mice at doses as low as 0.2 mg/kg.

  DOI：

  10.1021/jm800792b

文献信息

• A β-Fluoroamine Inhibitor of Purine Nucleoside Phosphorylase
  作者：Jennifer M. Mason、Andrew S. Murkin、Lei Li、Vern L. Schramm、Graeme J. Gainsford、Brian W. Skelton

  DOI：10.1021/jm800792b

  日期：2008.9.25

  The potent immucillin purine nucleoside phosphorylase (PNP) inhibitors F-DADMe-ImmH [(3S,4S)-3], and [(3R,4R)-3] are synthesized in seven steps. Cycloaddition to a fluoroalkene and an enzymic resolution are the key features of the construction of the fluoropyrrolidines 11, from which the immucillins are assembled by use of a three-component Mannich reaction. Slow-onset binding constants (K(i)*) for [(3S,4S)-3] and [(3R,4R)-3] with human PNP are 0.032 and 1.82 nM, respectively. F-DADMe-ImmH [(3S,4S)-3] exhibits oral availability in mice at doses as low as 0.2 mg/kg.