2-amino-6-chloro-9-<(1-benzyloxymethyl-3-diethylphosphono)-1-propyloxymethyl>-9H-purine | 156569-08-3

• 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: 2-amino-6-chloro-9-<(1-benzyloxymethyl-3-diethylphosphono)-1-propyloxymethyl>-9H-purine
• 英文别名: 6-Chloro-9-[(4-diethoxyphosphoryl-1-phenylmethoxybutan-2-yl)oxymethyl]purin-2-amine；6-chloro-9-[(4-diethoxyphosphoryl-1-phenylmethoxybutan-2-yl)oxymethyl]purin-2-amine
• CAS: 156569-08-3
• 化学式: C₂₁H₂₉ClN₅O₅P
• 分子量: 497.919
• InChiKey: JMVANHIAZZZMQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-9-<(1-benzyloxymethyl-3-diethylphosphono)-1-propyloxymethyl>-9H-purine 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 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  diethyl 4-O-benzyl-3,4-dihydroxybutylphosphonate 在 盐酸 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-amino-6-chloro-9-<(1-benzyloxymethyl-3-diethylphosphono)-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

• [EN] THERAPEUTIC NUCLEOSIDES
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：WO1993006112A1

  公开（公告）日：1993-04-01

  (EN) The present invention relates to an antiviral phosphonate derivate of an acyclic purine nucleoside analog, to pharmaceutically acceptable derivatives thereof and to their use in medical therapy, particularly in the treatment of cytomegalovirus infections. Methods for preparing the R-enantiomer of the compound of the invention, substantially free from the corresponding S-enantiomer are disclosed.(FR) La présente invention se rapporte à un dérivé de phosphonate antiviral d'un analogue de nucléoside de purine acyclique, à des dérivés pharmaceutiquement acceptables, ainsi qu'à leur utilisation en thérapie médicale, en particulier pour le traitement d'infections par cytomégalovirus. Des procédés de préparation de l'énantiomère-R du composé de l'invention, lequel est pratiquement dépourvu de l'énantiomère-S correspondant, sont également décrits.
• 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.