6-(4-isopropyl)phenylaminopurine | 1365348-70-4

• 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: 6-(4-isopropyl)phenylaminopurine
• 英文别名: N-(4-propan-2-ylphenyl)-7H-purin-6-amine
• CAS: 1365348-70-4
• 化学式: C₁₄H₁₅N₅
• 分子量: 253.307
• InChiKey: YZGDWVFRDCNCQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(4-isopropyl)phenylaminopurine 、 (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 1,4-二氧六环 为溶剂， 以39%的产率得到N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-6-(4-isopropyl)phenylaminopurine
  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：

  4-异丙基苯胺 、 6-氯嘌呤 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 16.0h， 以88%的产率得到6-(4-isopropyl)phenylaminopurine
  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

• [EN] NOVEL ANTIVIRAL ACYCLIC NUCLEOSIDE PHOSPHONATES<br/>[FR] NOUVEAUX PHOSPHONATES DE NUCLÉOSIDES ACYCLIQUES ANTIVIRAUX
  申请人：CENTRE NAT RECH SCIENT

  公开号：WO2012034719A1

  公开（公告）日：2012-03-22

  Compounds of formula (I) wherein A represents a nucleobase or a derivative thereof, n is equal to 0 or 1 and R', R" are carbonic chain, and R10 is hydrogen or a carbonic chain for their use as antiviral agents.

  式(I)中A代表核碱基或其衍生物，n等于0或1，R'、R"为碳链，R10为氢或碳链，用作抗病毒剂。
• NOVEL ANTIVIRAL ACYCLIC NUCLEOSIDE PHOSPHONATES
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2616474A1

  公开（公告）日：2013-07-24
• 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.