acyclovir P-(O-isopropyl) hydrogenphosphonate | 661465-32-3

• 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: acyclovir P-(O-isopropyl) hydrogenphosphonate
• 英文别名: acyclovir O-isopropyl phosphite；2-amino-9-(2-propan-2-yloxyphosphonoyloxyethoxymethyl)-3H-purin-6-one
• CAS: 661465-32-3
• 化学式: C₁₁H₁₈N₅O₅P
• 分子量: 331.268
• InChiKey: RIOMKTLGNDRPIH-UHFFFAOYSA-N

物化性质

• 沸点：
  590.4±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.51
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134.35
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  acyclovir P-(O-isopropyl) hydrogenphosphonate 在 human blood serum 作用下， 以 水 为溶剂， 反应 72.0h， 以52%的产率得到阿昔洛韦
  参考文献：
  名称：

  Synthesis and Antiherpetic Activity of Acyclovir Phosphonates

  摘要：

  Phosphonate derivatives of acyclovir containing phosphorous acid and ethoxy-carbonylphosphonic acid residues as well as their isopropyl esters were prepared. They selectively inhibited the herpes simplex virus 1 reproduction in Vero cell culture, the efficacy of esters being 3-4 times higher than that of ACV. The hydrolysis of the synthesized compounds was studied in the PBS buffer and human blood serum.

  DOI：

  10.1081/ncn-120021431
• 作为产物：
  描述：

  异丙醇 、 acyclovir hydrogenphosphonate 在 吡啶 、 三甲基乙酰氯 作用下， 以56%的产率得到acyclovir P-(O-isopropyl) hydrogenphosphonate
  参考文献：
  名称：

  Synthesis and Antiherpetic Activity of Acyclovir Phosphonates

  摘要：

  Phosphonate derivatives of acyclovir containing phosphorous acid and ethoxy-carbonylphosphonic acid residues as well as their isopropyl esters were prepared. They selectively inhibited the herpes simplex virus 1 reproduction in Vero cell culture, the efficacy of esters being 3-4 times higher than that of ACV. The hydrolysis of the synthesized compounds was studied in the PBS buffer and human blood serum.

  DOI：

  10.1081/ncn-120021431

文献信息

• The Synthesis and Antiherpetic Activity of Acyclovir Phosphonate Esters
  作者：M. V. Jasko、N. Yu. Ulanova、V. L. Andronova、A. V. Ivanov、I. L. Karpenko、M. K. Kukhanova、G. A. Galegov、Yu. S. Skoblov

  DOI：10.1023/b:rubi.0000049770.51092.76

  日期：2004.11

  Alkyl esters of acyclovir phosphite, alkoxycarbonylphosphonate, ethoxycarbonylmethylphosphonate, and aminocarbonylphosphonate were synthesized. Most of them were shown to inhibit the replication of type I herpes simplex virus in Vero cell culture. The stability in phosphate buffer and human blood serum was studied for several of the derivatives. A correlation between the stability and antiviral activity of the synthesized compounds is discussed.