2-amino-9-benzyl-6-ethylthio-8-hydroxypurine | 565473-16-7

• 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-9-benzyl-6-ethylthio-8-hydroxypurine
• 英文别名: 2-amino-9-benzyl-6-ethylsulfanyl-7H-purin-8-one
• CAS: 565473-16-7
• 化学式: C₁₄H₁₅N₅OS
• 分子量: 301.372
• InChiKey: HHGCBICBLHKUGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-9-benzyl-6-ethylthio-8-hydroxypurine 在 ammonium hydroxide 、 镍 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以61%的产率得到2-amino-9-benzyl-8-hydroxypurine
  参考文献：
  名称：

  Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers

  摘要：

  Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine (9) indicated the most potent activity with MEC of 0.001 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00234-7
• 作为产物：
  描述：

  4-amino-3-benzyl-2-oxo-1H-imidazole-5-carbonitrile 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 103.0h， 生成 2-amino-9-benzyl-6-ethylthio-8-hydroxypurine
  参考文献：
  名称：

  Efficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives

  摘要：

  一种高效且通用的方法被实现，用于合成预期具有多种生物活性的2,9-二取代的8-羟基腺苷。5-氨基-4-氰基-2-羟基咪唑（1）是从氨基丙腈和异氰酸酯作为关键中间体制备的。将1a与氨基脲、咪唑、胍、尿素和硫脲缩合，得到在2位具有各种取代基的8-羟基腺苷（2–6）。此外，对2-氨基和2-羟基腺苷（4和6）进行选择性烷基化，顺利实现，分别得到相应的2-烷基氨基和2-烷氧腺苷（5和7）。2-烷基硫腺苷（15）是通过1a与苯甲酰异硫氰酸酯的类似反应以及随后S-烷基化制备的。咪唑类化合物1是合成8-羟基腺苷衍生物最有用的中间体。

  DOI：

  10.1039/b300557g

文献信息

• Efficient synthesis of 2,9-disubstituted 8-hydroxyadenine derivatives
  作者：Kosaku Hirota、Kazunori Kazaoka、Itaru Niimoto、Hironao Sajiki

  DOI：10.1039/b300557g

  日期：2003.4.14

  An efficient and general method for the synthesis of 2,9-disubstituted 8-hydroxyadenines, which are expected to have various biological activities, was realized. 5-Amino-4-cyano-2-hydroxyimidazoles (1) were prepared from aminomalononitrile and isocyanates as key intermediates. The condensation of 1a with amidines, imidates, guanidine, urea and thioureas afforded 8-hydroxyadenines (2–6) possessing various substituents at the 2-position. Furthermore, selective alkylation of 2-amino- and 2-hydroxyadenines (4 and 6) successively proceeded to give the corresponding 2-alkylamino- and 2-alkoxyadenines (5 and 7), respectively. 2-Alkylthioadenines (15) were prepared by an analogous reaction of 1a with benzoyl isothiocyanate and subsequent S-alkylation. The imidazoles 1 are most useful intermediates for the synthesis of 8-hydroxyadenine derivatives.

  一种高效且通用的方法被实现，用于合成预期具有多种生物活性的2,9-二取代的8-羟基腺苷。5-氨基-4-氰基-2-羟基咪唑（1）是从氨基丙腈和异氰酸酯作为关键中间体制备的。将1a与氨基脲、咪唑、胍、尿素和硫脲缩合，得到在2位具有各种取代基的8-羟基腺苷（2–6）。此外，对2-氨基和2-羟基腺苷（4和6）进行选择性烷基化，顺利实现，分别得到相应的2-烷基氨基和2-烷氧腺苷（5和7）。2-烷基硫腺苷（15）是通过1a与苯甲酰异硫氰酸酯的类似反应以及随后S-烷基化制备的。咪唑类化合物1是合成8-羟基腺苷衍生物最有用的中间体。
• Synthesis and biological evaluation of 2,8-disubstituted 9-benzyladenines: discovery of 8-mercaptoadenines as potent interferon-inducers
  作者：Kosaku Hirota、Kazunori Kazaoka、Hironao Sajiki

  DOI：10.1016/s0968-0896(03)00234-7

  日期：2003.7

  Recently, we have identified 9-benzyl-8-hydroxyadenines bearing an appropriate substituent (a butoxy, propylthio or butylamino group) at the 2-position as potent interferon (IFN)-inducers. Herein we report the design, synthesis, and IFN-inducing activity of 8-substituted 9-benzyladenines possessing such an appropriate substituent at the 2-position. Introduction of the appropriate substituent into the 2-position of the adenine nucleus gave rise to expression of the activity even in 9-benzyladenines bearing no hydroxyl group at the 8-position. An amino group at the 6-position and a hydroxyl or thiol group carrying an acidic proton at the 8-position are required to express excellent IFN-inducing activity. 9-Benzyl-2-butoxy-8-mercaptoadenine (9) indicated the most potent activity with MEC of 0.001 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.