(E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate | 1415634-04-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate
• 英文别名: [2,2-dimethylpropanoyloxymethoxy-[(E)-4-hydroxybut-2-enyl]phosphoryl]oxymethyl 2,2-dimethylpropanoate
• CAS: 1415634-04-6
• 化学式: C₁₆H₂₉O₈P
• 分子量: 380.375
• InChiKey: DWCWWKNZKVJPNN-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate 在 甲酸 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 20.0h， 生成 N9-(4'-bis(POM)-phosphinylbut-2'-enyl)guanine
  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
• 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) 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 96.0h， 生成 (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate
  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

• PHOSPHONATES SYNTHONS FOR THE SYNTHESIS OF PHOSPHONATES DERIVATIVES SHOWING BETTER BIOAVAILABILITY
  申请人：Agrofoglio Luigi A.

  公开号：US20120142897A1

  公开（公告）日：2012-06-07

  Synthons for the synthesis of phosphonates prodrugs POM and POC, especially for direct Cross Metathesis.
• US8785629B2
  申请人：——

  公开号：US8785629B2

  公开（公告）日：2014-07-22
• 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.