9-benzyl-2-(p-tolyl)-8-azaadenine | 112633-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 9-benzyl-2-(p-tolyl)-8-azaadenine
• 英文别名: 3-Benzyl-5-(4-methylphenyl)triazolo[4,5-d]pyrimidin-7-amine
• CAS: 112633-77-9
• 化学式: C₁₈H₁₆N₆
• 分子量: 316.365
• InChiKey: DAHUWMQTIIEVQP-UHFFFAOYSA-N

物化性质

• 沸点：
  490.0±45.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  82.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-benzyl-2-(p-tolyl)-8-azaadenine 、 4-三氟甲基苯基异氰酸酯 以 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到
  参考文献：
  名称：

  2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies

  摘要：

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.063
• 作为产物：
  描述：

  5-氨基-1-苄基-1H-1,2,3-噻唑-4-羧胺 在 氨 、 N,N-二乙基苯胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 9-benzyl-2-(p-tolyl)-8-azaadenine
  参考文献：
  名称：

  2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies

  摘要：

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.063

文献信息

• “One pot” synthesis of 2,9-disubstituted 8-azaadenines (3,5-disubstituted 7-amino-3<i>H</i>-1,2,3-triazolo[4,5-<i>d</i>]pyrimidines)
  作者：Pier Luigi Barili、Giuliana Biagi、Oreste Livi、Luciana Mucci、Valerio Scartoni

  DOI：10.1002/jhet.5570240419

  日期：1987.7

  A new simple method for the synthesis of title compounds is described starting from malononitrile, benzyl-azide and an aliphatic or aromatic nitrile.

  从丙二腈，苄基叠氮化物和脂族或芳族腈开始，描述了一种用于标题化合物合成的新的简单方法。
• BARILI, PIER LUIGI;BIAGI, GIULIANA;LIVI, ORESTE;MUCCI, LUCIANA;SCARTONI, +, J. HETEROCYCL. CHEM., 24,(1987) N 4, 997-1001
  作者：BARILI, PIER LUIGI、BIAGI, GIULIANA、LIVI, ORESTE、MUCCI, LUCIANA、SCARTONI, +

  DOI：——

  日期：——
• 2,9-Disubstituted-N6-(arylcarbamoyl)-8-azaadenines as new selective A3 adenosine receptor antagonists: Synthesis, biochemical and molecular modelling studies
  作者：Giuliana Biagi、Anna Maria Bianucci、Alessio Coi、Barbara Costa、Laura Fabbrini、Irene Giorgi、Oreste Livi、Iolanda Micco、Federica Pacchini、Edoardo Santini、Michele Leonardi、Fatena Ahmad Nofal、Oreste LeRoy Salerni、Valerio Scartoni

  DOI：10.1016/j.bmc.2005.04.063

  日期：2005.8

  A number of N-6-(N-arylcarbamoyl)-2-substituted-9-benzyl-8-azaadenines, obtained by a modification of the synthetic scheme used to prepare selective A(1) ligands, by only three or two steps, are described. At first we prepared a series of 2-phenyl-9-benzyl-8-azaadenines having as N-6 substituent a variously substituted N-phenylcarbamoyl group. Some of these derivatives demonstrated good affinity towards the A(3) subtype but low selectivity. Compounds having p-CF3, p-F and p-OCH3, as substituents on the phenylcarbamoyl group were selected as lead compounds for the second part of this study. Without modifying the N-6 substituent, which would assure A(3) affinity, we varied the 9 and 2 positions on these molecules to enhance selectivity. Some compounds having a p-methyl group on the 2-phenyl substituent showed a very good affinity and selectivity for the A(3) subtype, revealing the first class of A(3) adenosine receptor selective antagonists with a bicyclic structure strictly correlated to the adenine nucleus. The molecular modelling work, carried out using the DOCK program, supplied two models which may be useful for a better understanding of the binding modes. Both models highlighted the preferred interacting tautomeric forms of the antagonists for human A(1) and A(3) receptors. (c) 2005 Elsevier Ltd. All rights reserved.

表征谱图