7-methyl-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine | 72966-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 7-methyl-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
• 英文别名: 7-Methyl-5-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
• CAS: 72966-18-8
• 化学式: C₁₂H₁₁N₅
• 分子量: 225.253
• InChiKey: UYHWZFMNTNPBCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-methyl-5-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine 、 4-丙氧基苯甲酰氯 在 吡啶 作用下， 以35%的产率得到N-(7-methyl-5-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-4-propoxybenzamide
  参考文献：
  名称：

  A Broad Anti-influenza Hybrid Small Molecule That Potently Disrupts the Interaction of Polymerase Acidic Protein–Basic Protein 1 (PA-PB1) Subunits

  摘要：

  In continuing our efforts to identify Small molecules able; to disrupt the interaction of the polymerase acidic protein-basic protein 1 (PA-PB1) subunits of Influenza Virus (Flu) RNA-dependent RNA polymerase, this paper is devoted to the optimization of a dihydrotriazolopyrimidine derivative, previously identified throught structure-based drug discovery. The structure modifications performed around the bicyclic core led to the identification of compounds endowed with both the ability to disrupt PA-PB1 subunits interaction and anti-Flu activity with no cytotoxicity. Very interesting results were obtained with the hybrid molecules 36 and 37, designed by merging some peculiar structural features known to impart PA-PB1 interaction inhibition, with compound 36 that emerged as the most potent PA-PB1 interaction inhibitor (IC50 = 1.1 mu M) among all the small molecules reported so far. Calculations Showed a very favoted H-bonding between the 2-amidic carbonyl of 36 and Q408, which seems to justify its potent ability to interfere with the interaction of the polymerase subunits.

  DOI：

  10.1021/acs.jmedchem.5b00012
• 作为产物：
  描述：

  Hydrazin-N.N'-dicarbonsaeure-diamidin 、 2-Buten-1-one, 3-hydroxy-1-phenyl-, (E)- 以28%的产率得到
  参考文献：
  名称：

  KREUTZBERGER A.; RISSE G., ARCH. PHARM., 1979, 312, NO 12, 1003-1006

  摘要：

  DOI：

文献信息

• Efficient and regioselective one-step synthesis of 7-aryl-5-methyl- and 5-aryl-7-methyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidine derivatives
  作者：Serena Massari、Jenny Desantis、Giulio Nannetti、Stefano Sabatini、Sara Tortorella、Laura Goracci、Violetta Cecchetti、Arianna Loregian、Oriana Tabarrini

  DOI：10.1039/c7ob02085f

  日期：——

  facile and efficient one-step procedures for the regioselective synthesis of 7-aryl-5-methyl- and 5-aryl-7-methyl-2-amino-[1,2,4]triazolo[1,5-a]pyrimidines have been developed, via reactions of 3,5-diamino-1,2,4-triazole with variously substituted 1-aryl-1,3-butanediones and 1-aryl-2-buten-1-ones, respectively. The excellent yield and/or regioselectivity shown by the reactions decreased when ethyl 5-amino-1

  区域选择性合成7-芳基-5-甲基-和5-芳基-7-甲基-2-氨基-[1,2,4]三唑并[1,5-a]嘧啶的两种简便有效的一步步骤通过3，5-二氨基-1，2，4-三唑分别与各种取代的1-芳基-1，3-丁二酮和1-芳基-2-丁烯-1-酮的反应，已经开发出。当使用5-氨基-1，2，4-三唑-3-羧酸乙酯时，反应显示的优异的产率和/或区域选择性降低。作为[1,2,4]三唑并[1,5-a]嘧啶的特有支架，本文报道的方法可用于制备生物活性化合物。在这项研究中，基于[1,2,4] triazolo [1，
• A Broad Anti-influenza Hybrid Small Molecule That Potently Disrupts the Interaction of Polymerase Acidic Protein–Basic Protein 1 (PA-PB1) Subunits
  作者：Serena Massari、Giulio Nannetti、Jenny Desantis、Giulia Muratore、Stefano Sabatini、Giuseppe Manfroni、Beatrice Mercorelli、Violetta Cecchetti、Giorgio Palù、Gabriele Cruciani、Arianna Loregian、Laura Goracci、Oriana Tabarrini

  DOI：10.1021/acs.jmedchem.5b00012

  日期：2015.5.14

  In continuing our efforts to identify Small molecules able; to disrupt the interaction of the polymerase acidic protein-basic protein 1 (PA-PB1) subunits of Influenza Virus (Flu) RNA-dependent RNA polymerase, this paper is devoted to the optimization of a dihydrotriazolopyrimidine derivative, previously identified throught structure-based drug discovery. The structure modifications performed around the bicyclic core led to the identification of compounds endowed with both the ability to disrupt PA-PB1 subunits interaction and anti-Flu activity with no cytotoxicity. Very interesting results were obtained with the hybrid molecules 36 and 37, designed by merging some peculiar structural features known to impart PA-PB1 interaction inhibition, with compound 36 that emerged as the most potent PA-PB1 interaction inhibitor (IC50 = 1.1 mu M) among all the small molecules reported so far. Calculations Showed a very favoted H-bonding between the 2-amidic carbonyl of 36 and Q408, which seems to justify its potent ability to interfere with the interaction of the polymerase subunits.
• KREUTZBERGER A.; RISSE G., ARCH. PHARM., 1979, 312, NO 12, 1003-1006
  作者：KREUTZBERGER A.、 RISSE G.

  DOI：——

  日期：——