N-(5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)acetamide | 935398-18-8

• 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: N-(5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)acetamide
• CAS: 935398-18-8
• 化学式: C₁₄H₁₃N₅O
• 分子量: 267.29
• InChiKey: FCPDWKVIBCCXQR-UHFFFAOYSA-N

物化性质

• 熔点：
  236-237 °C(Solv: N,N-dimethylformamide (68-12-2); ethanol (64-17-5))
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.18
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)acetamide 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.67h， 以94%的产率得到5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
  参考文献：
  名称：

  Improved synthesis of 2-amino-1,2,4-triazolo[1,5-a]pyrimidines

  摘要：

  An improved procedure is suggested for preparing 2-amino-1,2,4-triazolo[1,5-a]pyrimidines from 3,5-diamino-1,2,4-triazole and unsaturated aromatic ketones, with acetyl protection of the amino group in the step of oxidation of 2-amino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines.

  DOI：

  10.1134/s1070427206070172
• 作为产物：
  描述：

  2-amino-5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.63h， 生成 N-(5-methyl-7-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)acetamide
  参考文献：
  名称：

  Improved synthesis of 2-amino-1,2,4-triazolo[1,5-a]pyrimidines

  摘要：

  An improved procedure is suggested for preparing 2-amino-1,2,4-triazolo[1,5-a]pyrimidines from 3,5-diamino-1,2,4-triazole and unsaturated aromatic ketones, with acetyl protection of the amino group in the step of oxidation of 2-amino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines.

  DOI：

  10.1134/s1070427206070172

文献信息

• 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.