9-benzyl-2-phenyladenine | 640274-34-6

• 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: 9-benzyl-2-phenyladenine
• 英文别名: 9H-Purin-6-amine, 2-phenyl-9-(phenylmethyl)-；9-benzyl-2-phenylpurin-6-amine
• CAS: 640274-34-6
• 化学式: C₁₈H₁₅N₅
• 分子量: 301.351
• InChiKey: BEOSCMJDDJMLRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-phenyladenine 在 盐酸 、 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 10.0h， 生成 9-benzyl-8-hydroxy-2-phenyladenine
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 2-substituted-8-hydroxyadenine derivatives as orally available interferon inducers without emetic side effects

  摘要：

  Recently we reported the adenine derivatives (2-4) as new interferon (IFN) inducers. In the present study, we conducted a detailed structure and activity relationship study of 4 and its related derivatives on IFN inducing activity. From this study, we found that compound 4 exhibited the most potent IFN inducing activity in vitro with a minimum effective concentration of 0.01 muM, and 4 also showed strong IFN-inducing activity at doses of more than 0.3 mg/kg by oral administration in mice. This potency was 10-fold stronger than that of Imiquimod. Moreover, 4 did not cause emesis in ferrets even at doses as high as 10 mg/kg, whereas. 80% of animals, were emetic when orally administered with the same dose of Imiquimod. These results indicate that compound 4 is superior to Imiquimod with respect to efficacy and safety. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00369-9
• 作为产物：
  描述：

  4,6-二氯-2-苯基嘧啶-5-胺 在 氨 、 乙酸酐 、 N,N-二乙基苯胺 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 9-benzyl-2-phenyladenine
  参考文献：
  名称：

  N6-环烷基-2-苯基-3-deaza-8-azaadenines：一类新的A1腺苷受体配体。与相应的腺嘌呤和8-氮杂腺嘌呤的比较。

  摘要：

  几种9-苄基-N6-环烷基-2-苯基ade啶，9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤和4-环烷基氨基-1-苄基-6-苯基-1H-1,2,3-三唑制备[4，5-c]吡啶并测定为A1腺苷受体配体。1H-1,2,3-三唑并[4,5-c]吡啶是从N，N-二乙基-1-苄基-4-羧基酰胺基-5-甲基-1H-1,2,3-三唑开始得到的苯甲腈存在下，在无水四氢呋喃中进行锂化反应。通常的处理提供了分离的1-苄基-6-苯基-1H-1,2,3-三唑并[4,5-c]吡啶-4-酮，其用三氯氧磷和环烷基胺处理。一些化合物表现出高亲和力和选择性，Ki值的趋势对应于9-苄基-N6-环烷基-2-苯基ade啶和9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤的系列，因此它们可以是被认为是生物等排体。

  DOI：

  10.1016/j.ejmech.2003.09.003

文献信息

• Synthesis and structure–activity relationships of 2-substituted-8-hydroxyadenine derivatives as orally available interferon inducers without emetic side effects
  作者：Yoshiaki Isobe、Masanori Tobe、Haruhisa Ogita、Ayumu Kurimoto、Tetsuhiro Ogino、Hajime Kawakami、Haruo Takaku、Hironao Sajiki、Kosaku Hirota、Hideya Hayashi

  DOI：10.1016/s0968-0896(03)00369-9

  日期：2003.8

  Recently we reported the adenine derivatives (2-4) as new interferon (IFN) inducers. In the present study, we conducted a detailed structure and activity relationship study of 4 and its related derivatives on IFN inducing activity. From this study, we found that compound 4 exhibited the most potent IFN inducing activity in vitro with a minimum effective concentration of 0.01 muM, and 4 also showed strong IFN-inducing activity at doses of more than 0.3 mg/kg by oral administration in mice. This potency was 10-fold stronger than that of Imiquimod. Moreover, 4 did not cause emesis in ferrets even at doses as high as 10 mg/kg, whereas. 80% of animals, were emetic when orally administered with the same dose of Imiquimod. These results indicate that compound 4 is superior to Imiquimod with respect to efficacy and safety. (C) 2003 Elsevier Ltd. All rights reserved.
• N6-Cycloalkyl-2-phenyl-3-deaza-8-azaadenines: a new class of A1 adenosine receptor ligands. A comparison with the corresponding adenines and 8-azaadenines
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Antonio Nardi、Federica Pacchini、Valerio Scartoni、Antonio Lucacchini

  DOI：10.1016/j.ejmech.2003.09.003

  日期：2003.11

  -1,2,3-triazolo[4,5-c]pyridines were prepared and assayed as A1 adenosine receptor ligands. The 1H-1,2,3-triazolo[4,5-c]pyridines were obtained starting from N,N-diethyl-1-benzyl-4-carboxyamido-5-methyl-1H-1,2,3-triazole by lithiation in anhydrous tetrahydrofurane in the presence of benzonitrile. The usual work up afforded the isolation of 1-benzyl-6-phenyl-1H-1,2,3-triazolo[4,5-c]pyridin-4-one which

  几种9-苄基-N6-环烷基-2-苯基ade啶，9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤和4-环烷基氨基-1-苄基-6-苯基-1H-1,2,3-三唑制备[4，5-c]吡啶并测定为A1腺苷受体配体。1H-1,2,3-三唑并[4,5-c]吡啶是从N，N-二乙基-1-苄基-4-羧基酰胺基-5-甲基-1H-1,2,3-三唑开始得到的苯甲腈存在下，在无水四氢呋喃中进行锂化反应。通常的处理提供了分离的1-苄基-6-苯基-1H-1,2,3-三唑并[4,5-c]吡啶-4-酮，其用三氯氧磷和环烷基胺处理。一些化合物表现出高亲和力和选择性，Ki值的趋势对应于9-苄基-N6-环烷基-2-苯基ade啶和9-苄基-N6-环烷基-2-苯基-8-氮杂腺嘌呤的系列，因此它们可以是被认为是生物等排体。