N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-6-allylaminopurine | 1365348-46-4

• 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: N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-6-allylaminopurine
• 英文别名: [2,2-dimethylpropanoyloxymethoxy-[4-[6-(prop-2-enylamino)purin-9-yl]but-2-enyl]phosphoryl]oxymethyl 2,2-dimethylpropanoate
• CAS: 1365348-46-4
• 化学式: C₂₄H₃₆N₅O₇P
• 分子量: 537.553
• InChiKey: WVPSLZMQGNDPSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  37.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  143.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为产物：
  描述：

  烯丙基磷酸二甲酯 在 [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(benzylidene)(triphenylphosphine) ruthenium(II) 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 sodium iodide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 生成 N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-6-allylaminopurine
  参考文献：
  名称：

  Synthesis and antiviral evaluation of bis(POM) prodrugs of (E)-[4′-phosphono-but-2′-en-1′-yl]purine nucleosides

  摘要：

  Seventeen hitherto unknown bis(POM) prodrugs of novel (E)-[4'-phosphono-but-2'-en-1'-yl]purine nucleosides were prepared in a straight approach and at good yields. Those compounds were synthesized by the reaction of purine nucleobases directly with the phosphonate synthon 3 bearing POM biolabile groups under Mitsunobu conditions. All obtained compounds were evaluated for their antiviral activities against a large number of DNA and RNA viruses including herpes simplex viruses 1 and 2, varicella zoster virus, Feline herpes virus, human cytomegalovirus, HIV-1 and HIV-2. Among these molecules, some of them exhibit anti-VZV and anti-HIV activity at submicromolar concentrations. This class of compound will be of further interest for lead optimization as anti-infectious agents. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.08.042

文献信息

• Synthesis and antiviral evaluation of bis(POM) prodrugs of (E)-[4′-phosphono-but-2′-en-1′-yl]purine nucleosides
  作者：Ugo Pradère、Vincent Roy、Aurélien Montagu、Ozkan Sari、Manabu Hamada、Jan Balzarini、Robert Snoeck、Graciela Andrei、Luigi A. Agrofoglio

  DOI：10.1016/j.ejmech.2012.08.042

  日期：2012.11

  Seventeen hitherto unknown bis(POM) prodrugs of novel (E)-[4'-phosphono-but-2'-en-1'-yl]purine nucleosides were prepared in a straight approach and at good yields. Those compounds were synthesized by the reaction of purine nucleobases directly with the phosphonate synthon 3 bearing POM biolabile groups under Mitsunobu conditions. All obtained compounds were evaluated for their antiviral activities against a large number of DNA and RNA viruses including herpes simplex viruses 1 and 2, varicella zoster virus, Feline herpes virus, human cytomegalovirus, HIV-1 and HIV-2. Among these molecules, some of them exhibit anti-VZV and anti-HIV activity at submicromolar concentrations. This class of compound will be of further interest for lead optimization as anti-infectious agents. (C) 2012 Elsevier Masson SAS. All rights reserved.