2-amino-6-(butylamino)purine | 5437-50-3

• 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-(butylamino)purine
• 英文别名: 2-amino-6-n-butylaminopurine；6-N-butyl-7H-purine-2,6-diamine
• CAS: 5437-50-3
• 化学式: C₉H₁₄N₆
• 分子量: 206.25
• InChiKey: REMXDSRYVGKQHF-UHFFFAOYSA-N

物化性质

• 熔点：
  165-166 °C(Solv: chloroform (67-66-3))
• 沸点：
  344.9±52.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  92.5
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (E)-bis(POM)-4-hydroxy-but-2-en-1-yl phosphonate 、 2-amino-6-(butylamino)purine 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49%的产率得到N⁹-(4'-bis(POM)-phosphinylbut-2'-enyl)-2-amino-6-butylaminopurine
  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：

  正丁胺 、 2-氨基-6-氯嘌呤 反应 0.25h， 以84%的产率得到2-amino-6-(butylamino)purine
  参考文献：
  名称：

  在聚焦微波辐射下高效合成取代的胞嘧啶和嘌呤

  摘要：

  描述了在聚焦微波辐射下6-氯嘌呤，2-氨基-6-氯嘌呤和5-溴胞嘧啶与各种亲核试剂的快速亲核取代反应。使用这种方法，可以在较短的反应时间内获得高达99％的收率的所需产物。

  DOI：

  10.1016/j.tet.2007.02.124

文献信息

• Synthesis of Potential Anticancer Agents. XI. N^2,6-Alkyl Derivatives of 2,6-Diaminopurine²
  作者：John A. Montgomery、Lee B. Holum

  DOI：10.1021/ja01535a040

  日期：1958.1
• Solution-phase synthesis of 2,6,9-trisubstituted purines
  作者：Maria T. Fiorini、Chris Abell

  DOI：10.1016/s0040-4039(98)00098-7

  日期：1998.3

  A simple three-step method for the solution-phase combinatorial synthesis of 2,6,9-trisubstituted purines from 2,6-dichloropurine is described. The synthesis exploits the use of resin capture to remove excess reagent used in the final step. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An efficient synthesis of substituted cytosines and purines under focused microwave irradiation
  作者：Ling-Kuen Huang、Yen-Chih Cherng、Yann-Ru Cheng、Jing-Pei Jang、Yi-Ling Chao、Yie-Jia Cherng

  DOI：10.1016/j.tet.2007.02.124

  日期：2007.6

  A rapid nucleophilic displacement reaction of 6-chloropurine, 2-amino-6-chloropurine and 5-bromocytosine with various nucleophiles under focused microwave irradiation is described. Using this method, the desired products were obtained with the yields up to 99% in a short reaction time.

  描述了在聚焦微波辐射下6-氯嘌呤，2-氨基-6-氯嘌呤和5-溴胞嘧啶与各种亲核试剂的快速亲核取代反应。使用这种方法，可以在较短的反应时间内获得高达99％的收率的所需产物。
• 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.

表征谱图