4-Amino-1-benzyl-6-phenyl-1H-1,2,3-triazolo<4,5-d>pyrimidin | 94079-03-5

• 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: 4-Amino-1-benzyl-6-phenyl-1H-1,2,3-triazolo<4,5-d>pyrimidin
• 英文别名: 9-phenylmethyl-2-phenyl-8-azapurine；2-phenyl-9-benzyl-8-azaadenine；9-benzyl-2-phenyl-8-azaadenine；3-benzyl-5-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-amine；3-benzyl-5-phenyltriazolo[4,5-d]pyrimidin-7-amine
• CAS: 94079-03-5
• 化学式: C₁₇H₁₄N₆
• 分子量: 302.338
• InChiKey: MYSWGJASKRUDKS-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  482.2±37.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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：
  82.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  环戊基甲酰氯 、 4-Amino-1-benzyl-6-phenyl-1H-1,2,3-triazolo<4,5-d>pyrimidin 以 甲苯 为溶剂， 反应 24.0h， 以15%的产率得到N-(3-benzyl-5-phenyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)cyclopentanecarboxamide
  参考文献：
  名称：

  Synthesis, biological assays and QSAR studies of N-(9-benzyl-2-phenyl-8-azapurin-6-yl)-amides as ligands for A1 adenosine receptors

  摘要：

  2-Phenyl-9-benzyl-8-azapurines, bearing at the 6 position an amido group interposed between the 8-azapurine moiety and an alkyl or a substituted phenyl group, have been synthesised and assayed as ligands for adenosine receptors. All the compounds show high affinity for the A(1) adenosine receptor, and many of them also show a good selectivity for A(1) with respect to A(2)A and A(3) adenosine receptors. Based on the quite rich library containing such compounds and relevant biological data, QSAR models, able to rationalise the results and to give a quantitative estimate of the observed trends were also developed. The obtained models can assist in the design of new compounds selectively active on A(1) adenosine receptor. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.060
• 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 4-Amino-1-benzyl-6-phenyl-1H-1,2,3-triazolo<4,5-d>pyrimidin
  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

• Preparation of new N⁶, 9-disubstituted 2-phenyl-adenines and corresponding 8-azaadenines.: A feasibility study for application to solid-phase Synthesis. I
  作者：Giuliana Biagi、Irene Giorgi、Oreste Livi、Federica Pacchini、Valerio Scartoni、Oreste Leroy Salerni

  DOI：10.1002/jhet.5570410415

  日期：2004.7

  group by oxidation with m-chloroperoxybenzoic acid affording purines 15–18 and their 8-azaanalogs 19–21; these compounds, as crude products, were treated with an amine to yield the corresponding adenines 22–25 or 8-azaadenines 26–31. All reactions were performed under conditions com patible with the possible use of a thiomethyl resin in place of phenylmethanethiol to bind the pyrimidine ring of 1 to a

  将适当取代的嘧啶1转化为许多标题化合物。取决于反应温度，通过用苯甲硫醇处理，在1中包含氯原子的亲核取代产生2或3。用胺处理3得到6-苯基甲硫基-N 4-取代的-2-苯基-嘧啶-4,5-二胺4-7。这些嘧啶被转化为2-苯基嘌呤8-11和2-苯基-8-氮杂嘌呤12-14通过在盐酸（或乙酸酐）存在下用原甲酸三乙酯处理，或分别用亚硝酸钾和乙酸处理。上C（6）硫醚函数然后用转化成磺酰基通过氧化米氯过氧苯甲酸，得到嘌呤15-18和它们的8 azaanalogs 19-21 ; 这些化合物作为粗产物用胺处理，得到相应的腺嘌呤22–25或8-氮杂腺嘌呤26–31。所有反应均在与可能使用硫代甲基树脂代替苯基甲硫醇以使1的嘧啶环与固相结合的条件下进行。
• “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。
• Korbonits, Dezsoe; Kiss, Pal; Simon, Kalman, Chemische Berichte, 1984, vol. 117, # 11, p. 3183 - 3193
  作者：Korbonits, Dezsoe、Kiss, Pal、Simon, Kalman、Kolonits, Pal

  DOI：——

  日期：——
• Biagi; Giorgi; Livi, Il Farmaco, 1995, vol. 50, # 10, p. 659 - 667
  作者：Biagi、Giorgi、Livi、Scartoni、Breschi、Martini、Scatizzi

  DOI：——

  日期：——
• Biagi; Giorgi; Livi, Il Farmaco, 1994, vol. 49, # 3, p. 187 - 191
  作者：Biagi、Giorgi、Livi、Scartoni、Lucacchini、Martini、Tacchi

  DOI：——

  日期：——