2-amino-9-([2-(chloromethyl)-2-oxo-1,3,2λ⁵-dioxaphosphinan-5-yl]oxymethyl)-6,9-dihydro-1H-6-purinone | 1473358-88-1

• 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: 2-amino-9-([2-(chloromethyl)-2-oxo-1,3,2λ⁵-dioxaphosphinan-5-yl]oxymethyl)-6,9-dihydro-1H-6-purinone
• 英文别名: 2-Amino-9-([2-(chloromethyl)-2-oxo-1,3,2lambda 5-dioxaphosphinan-5-yl]oxymethyl)-6,9-dihydro-1h-6-purinone；2-amino-9-[[2-(chloromethyl)-2-oxo-1,3,2λ5-dioxaphosphinan-5-yl]oxymethyl]-1H-purin-6-one
• CAS: 1473358-88-1
• 化学式: C₁₀H₁₃ClN₅O₅P
• 分子量: 349.67
• InChiKey: QOZFEUHCYOURKM-UHFFFAOYSA-N

物化性质

• 沸点：
  647.5±65.0 °C(predicted)
• 密度：
  2.01±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-氨基-2-苯乙酸乙酯 、 2-amino-9-([2-(chloromethyl)-2-oxo-1,3,2λ⁵-dioxaphosphinan-5-yl]oxymethyl)-6,9-dihydro-1H-6-purinone 以 四氢呋喃 、 吡啶 为溶剂， 反应 4.0h， 生成 ethyl 2-[(5-[(2-amino-6-oxo-6,9-dihydro-1H-9-purinyl)methoxy]-2-oxo-1,3,2λ⁵-dioxaphosphinan-2-ylmethyl)amino]-2-phenylacetate
  参考文献：
  名称：

  Phosphorylated ganciclovir derivatives: design, synthesis and in vitro and in vivo immunomodulatory activity

  摘要：

  Synthesis of a series of novel phosphorylated ganciclovir derivatives with bioactive amines/aminoacid esters as substituents was accomplished. These compounds were structurally characterized by IR, NMR (H-1, C-13, P-31), mass spectra and CHN analysis. The compounds (5a-m) have been evaluated for its in vitro and in vivo immunomodulatory activities. The amino acid ester-substituted ganciclovir derivatives, especially the 5g and 5i, increased the intracellular killing activity of the stimulated neutrophils. The in vivo experiment results show that the administration of compounds 5g and 5i (8 mg/kg body weight) to diet-induced immune impaired obese rats ameliorated the significant increase in immune cell counts (lymphocytes, neutrophils and monocytes). In addition, TNF-alpha, IL-6 and IL-1 secretions were considerably restored to normal by the compounds 5g and 5i with regulation in the release of C-reactive protein suggesting their potentiating effect on immune system dysfunction. These in vitro and in vivo results suggest that the phosphorylated ganciclovir derivatives 5g and 5i are strong immunomodulators.

  DOI：

  10.1007/s00044-013-0819-6
• 作为产物：
  描述：

  更昔洛韦 、 氯甲基膦酸二氯化物 在 四甲基胍 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.25h， 生成 2-amino-9-([2-(chloromethyl)-2-oxo-1,3,2λ⁵-dioxaphosphinan-5-yl]oxymethyl)-6,9-dihydro-1H-6-purinone
  参考文献：
  名称：

  Phosphorylated ganciclovir derivatives: design, synthesis and in vitro and in vivo immunomodulatory activity

  摘要：

  Synthesis of a series of novel phosphorylated ganciclovir derivatives with bioactive amines/aminoacid esters as substituents was accomplished. These compounds were structurally characterized by IR, NMR (H-1, C-13, P-31), mass spectra and CHN analysis. The compounds (5a-m) have been evaluated for its in vitro and in vivo immunomodulatory activities. The amino acid ester-substituted ganciclovir derivatives, especially the 5g and 5i, increased the intracellular killing activity of the stimulated neutrophils. The in vivo experiment results show that the administration of compounds 5g and 5i (8 mg/kg body weight) to diet-induced immune impaired obese rats ameliorated the significant increase in immune cell counts (lymphocytes, neutrophils and monocytes). In addition, TNF-alpha, IL-6 and IL-1 secretions were considerably restored to normal by the compounds 5g and 5i with regulation in the release of C-reactive protein suggesting their potentiating effect on immune system dysfunction. These in vitro and in vivo results suggest that the phosphorylated ganciclovir derivatives 5g and 5i are strong immunomodulators.

  DOI：

  10.1007/s00044-013-0819-6