2-amino-6-hydroxyethylthio-9-<(1-benzyloxymethyl-3-phosphono)-1-propyloxymethyl>-9H-purine | 156569-12-9

• 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-amino-6-hydroxyethylthio-9-<(1-benzyloxymethyl-3-phosphono)-1-propyloxymethyl>-9H-purine
• 英文别名: [3-[[2-Amino-6-(2-hydroxyethylsulfanyl)purin-9-yl]methoxy]-4-phenylmethoxybutyl]phosphonic acid
• CAS: 156569-12-9
• 化学式: C₁₉H₂₆N₅O₆PS
• 分子量: 483.485
• InChiKey: WTMFJMKWTWJXJI-UHFFFAOYSA-N

物化性质

• 沸点：
  822.8±75.0 °C(predicted)
• 密度：
  1.55±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  32
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  191
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-amino-6-hydroxyethylthio-9-<(1-benzyloxymethyl-3-phosphono)-1-propyloxymethyl>-9H-purine 在 N,N'-二环己基-4-吗啉脒 、 palladium dihydroxide 、 sodium methylate 、 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 甲醇 、 乙醇 、 水 、 环己烯 为溶剂， 反应 22.0h， 生成 SR 3759
  参考文献：
  名称：

  Synthesis of Acyclonucleoside Phosphonates as Antiviral Agents Against Cytomegalovirus

  摘要：

  Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine. and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.

  DOI：

  10.1080/15257779408013261
• 作为产物：
  描述：

  (4-Benzyloxy-3-chloromethoxy-butyl)-phosphonic acid diethyl ester 在 三甲基溴硅烷 、 sodium methylate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-amino-6-hydroxyethylthio-9-<(1-benzyloxymethyl-3-phosphono)-1-propyloxymethyl>-9H-purine
  参考文献：
  名称：

  Synthesis of Acyclonucleoside Phosphonates as Antiviral Agents Against Cytomegalovirus

  摘要：

  Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine. and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.

  DOI：

  10.1080/15257779408013261

文献信息

• Synthesis of Acyclonucleoside Phosphonates as Antiviral Agents Against Cytomegalovirus
  作者：Elmer J. Reist、Wallace W. Bradford、Beatrice L. Ruhland-Fritsch、Priscilla A. Sturm、Nurulain T. Zaveri、John Huffman、Robert W. Sidwell

  DOI：10.1080/15257779408013261

  日期：1994.3

  Phosphonic acid analogs of ACV and DHPG that are isosteric with ACV phosphate and DHPG phosphate have been synthesized and evaluated for antiviral activity against human, murine. and guinea pig strains of cytomegalovirus. The phosphonates showed high activity against all of the strains. They were also evaluated against a DHPG resistant strain of human cytomegalovirus. Although the activity dropped considerably, significant antiviral activity was still evident.