2-(4-biphenyl)-8-methyl-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine | 1191274-88-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(4-biphenyl)-8-methyl-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine
• 英文别名: 11-Methyl-4-(4-phenylphenyl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaene；11-methyl-4-(4-phenylphenyl)-3,5,6,8,10,11-hexazatricyclo[7.3.0.02,6]dodeca-1(12),2,4,7,9-pentaene
• CAS: 1191274-88-0
• 化学式: C₁₉H₁₄N₆
• 分子量: 326.36
• InChiKey: PZKOWORCZOHDDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  60.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-biphenyl)-8-methyl-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 生成 N-(2-(4-biphenyl)-8-methylpyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-yl)-N'-(4-methoxyphenyl)-urea
  参考文献：
  名称：

  Does the combination of optimal substitutions at the C2-, N5- and N8-positions of the pyrazolo-triazolo-pyrimidine scaffold guarantee selective modulation of the human A3 adenosine receptors?

  摘要：

  In an attempt to study the optimal combination of a phenyl ring at the C-2-position and different substituents at the N-5- and N-8-positions towards the selective modulation of human A(3) adenosine receptors (hA(3)AR), we synthesized a new series of 2-para-(un)substituted-phenyl-pyrazolo-triazolo-pyrimidines bearing either a methyl or phenylethyl at N-8 and chains of variable length at N-5. Through biological evaluation, it was found that the majority of the compounds had good affinities towards the hA(3)AR in the low nanomolar range. Compound 16 possessed the best hA(3)AR affinity and selectivity profile (K(i)hA(3) = 1.33 nM; hA(1)/hA(3) = 4880; hA(2A)/hA(3) = 1100) in the present series of2-(substituted)phenylpyrazolo-triazolo-pyrimidine derivatives. In addition to pharmacological characterization, a molecular modeling investigation on these compounds further elucidated the effect of different substituents at the pyrazolo-triazolo-pyrimidine scaffold on affinity and selectivity to hA3AR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.026
• 作为产物：
  描述：

  1-甲基-3-氨基-4-氰基吡唑 在 碘苯二乙酸 、 三乙胺 、 肼 作用下， 生成 2-(4-biphenyl)-8-methyl-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine
  参考文献：
  名称：

  Does the combination of optimal substitutions at the C2-, N5- and N8-positions of the pyrazolo-triazolo-pyrimidine scaffold guarantee selective modulation of the human A3 adenosine receptors?

  摘要：

  In an attempt to study the optimal combination of a phenyl ring at the C-2-position and different substituents at the N-5- and N-8-positions towards the selective modulation of human A(3) adenosine receptors (hA(3)AR), we synthesized a new series of 2-para-(un)substituted-phenyl-pyrazolo-triazolo-pyrimidines bearing either a methyl or phenylethyl at N-8 and chains of variable length at N-5. Through biological evaluation, it was found that the majority of the compounds had good affinities towards the hA(3)AR in the low nanomolar range. Compound 16 possessed the best hA(3)AR affinity and selectivity profile (K(i)hA(3) = 1.33 nM; hA(1)/hA(3) = 4880; hA(2A)/hA(3) = 1100) in the present series of2-(substituted)phenylpyrazolo-triazolo-pyrimidine derivatives. In addition to pharmacological characterization, a molecular modeling investigation on these compounds further elucidated the effect of different substituents at the pyrazolo-triazolo-pyrimidine scaffold on affinity and selectivity to hA3AR. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.026

文献信息

• A new synthesis of 2,8-disubstituted pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidines
  作者：Anton V. Dolzhenko、Giorgia Pastorin、Anna V. Dolzhenko、Wai Keung Chui

  DOI：10.1016/j.tetlet.2009.07.113

  日期：2009.10

  5-c]pyrimidines, which are key intermediates in the preparation of adenosine receptor antagonists, is developed. The method allows introduction of a variety of aryl substituents at position 2 of the pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine system via cyclocondensation of 5-amino-4-iminopyrazolo[3,4-d]pyrimidine with benzaldehydes accompanied with oxidation by iodobenzene diacetate. Some unexpected

  开发了实用的吡唑并[4,3- e ] [1,2,4]三唑并[1,5- c ]嘧啶的合成方法，它们是制备腺苷受体拮抗剂的关键中间体。该方法允许通过5-氨基-4-亚氨基吡唑并环缩合在吡唑并[4,3- e ] [1,2,4]三唑并[1,5- c ]嘧啶体系的2位引入各种芳基取代基。[3,4- d ]嘧啶与苯甲醛并伴随有碘代二苯乙酸酯的氧化。观察到一些意想不到的反应，并使用NMR光谱和X射线晶体学证实了产物的结构。