2-(6-Aminopurin-9-yl)ethoxymethyl-[3-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]propoxy]phosphinic acid | 1334143-77-9

• 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: 2-(6-Aminopurin-9-yl)ethoxymethyl-[3-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]propoxy]phosphinic acid
• CAS: 1334143-77-9
• 化学式: C₂₄H₃₄N₅O₆P
• 分子量: 519.538
• InChiKey: AQQWCTKJXNDFFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  36
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  布洛芬 在 N,N'-二环己基-4-吗啉脒 、 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(6-Aminopurin-9-yl)ethoxymethyl-[3-[2-[4-(2-methylpropyl)phenyl]propanoyloxy]propoxy]phosphinic acid
  参考文献：
  名称：

  Synthesis, anti-HBV activity and renal cell toxicity evaluation of mixed phosphonate prodrugs of adefovir

  摘要：

  A series of phosphonate ester prodrugs of adefovir incorporating L-amino (thio)acid and non-steroidal anti-inflammatory drug (NSAID) moieties were synthesized and their anti-HBV activity and renal cell toxicity were evaluated in HepG2 2.2.15 and HK-2 cells respectively. Bioactivity evaluation results revealed that this kind of adefovir prodrug have lower renal cell toxicity than adefovir dipivoxil. Compounds 8a and 8b, incorporating the NSAID ketoprofen and the L-amino acid (Val or Ile) structural fragments, exhibited more potent anti-HBV activity than adefovir dipivoxil with IC50 = 0.51 and 0.73 mu M, SI = 1697.64 and 881.92 respectively. In vitro stability studies showed that the synthesized prodrugs have higher chemical and plasma stability than the positive control adefovir dipivoxil. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.013

文献信息

• Synthesis, anti-HBV activity and renal cell toxicity evaluation of mixed phosphonate prodrugs of adefovir
  作者：Xiao-Zhong Fu、Yu Ou、Jian-Ying Pei、Ying Liu、Jing Li、Wen Zhou、Yan-Yu Lan、Ai-Min Wang、Yong-Lin Wang

  DOI：10.1016/j.ejmech.2012.01.013

  日期：2012.3

  A series of phosphonate ester prodrugs of adefovir incorporating L-amino (thio)acid and non-steroidal anti-inflammatory drug (NSAID) moieties were synthesized and their anti-HBV activity and renal cell toxicity were evaluated in HepG2 2.2.15 and HK-2 cells respectively. Bioactivity evaluation results revealed that this kind of adefovir prodrug have lower renal cell toxicity than adefovir dipivoxil. Compounds 8a and 8b, incorporating the NSAID ketoprofen and the L-amino acid (Val or Ile) structural fragments, exhibited more potent anti-HBV activity than adefovir dipivoxil with IC50 = 0.51 and 0.73 mu M, SI = 1697.64 and 881.92 respectively. In vitro stability studies showed that the synthesized prodrugs have higher chemical and plasma stability than the positive control adefovir dipivoxil. (C) 2012 Elsevier Masson SAS. All rights reserved.