Propionic acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-butyl ester | 125080-65-1

• 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: Propionic acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-butyl ester
• 英文别名: [4-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)butyl] propanoate
• CAS: 125080-65-1
• 化学式: C₁₃H₁₉N₅O₄
• 分子量: 309.325
• InChiKey: NPRVLLVPTRGTPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Propionic acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-butyl ester 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 (S)-2-Amino-3-methyl-butyric acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-propionyloxymethyl-butyl ester; hydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of amino acid ester prodrugs of penciclovir

  摘要：

  The synthesis, aqueous solubility and stability, in vitro antiviral activity, and oral bioavailability of the amino acid ester prodrugs of penciclovir, 13-20, 23, and 24, are described. All of the prodrugs were highly soluble (>100 mg/mL) and sufficiently stable in aqueous solution. The oral bioavailability of O-acetyl-O-L-valylpenciclovir (13) (34%) in mice was comparable to that of famciclovir (33%) and approximately 4-fold higher than that of penciclovir. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00329-0
• 作为产物：
  描述：

  丙酸酐 、 penciclovir 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以43%的产率得到Propionic acid 4-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-2-hydroxymethyl-butyl ester
  参考文献：
  名称：

  Synthesis and evaluation of amino acid ester prodrugs of penciclovir

  摘要：

  The synthesis, aqueous solubility and stability, in vitro antiviral activity, and oral bioavailability of the amino acid ester prodrugs of penciclovir, 13-20, 23, and 24, are described. All of the prodrugs were highly soluble (>100 mg/mL) and sufficiently stable in aqueous solution. The oral bioavailability of O-acetyl-O-L-valylpenciclovir (13) (34%) in mice was comparable to that of famciclovir (33%) and approximately 4-fold higher than that of penciclovir. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00329-0

文献信息

• Synthesis and evaluation of amino acid ester prodrugs of penciclovir
  作者：Dae-Kee Kim、Namkyu Lee、Guang Jin Im、Young-Woo Kim、Kieyoung Chang、Hun-Taek Kim、Yong-Baik Cho、Won-Son Choi、Inho Jung、Key H. Kim

  DOI：10.1016/0960-894x(96)00329-0

  日期：1996.8

  The synthesis, aqueous solubility and stability, in vitro antiviral activity, and oral bioavailability of the amino acid ester prodrugs of penciclovir, 13-20, 23, and 24, are described. All of the prodrugs were highly soluble (>100 mg/mL) and sufficiently stable in aqueous solution. The oral bioavailability of O-acetyl-O-L-valylpenciclovir (13) (34%) in mice was comparable to that of famciclovir (33%) and approximately 4-fold higher than that of penciclovir. Copyright (C) 1996 Elsevier Science Ltd