2-amino-5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine | 148612-47-9

• 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: 2-amino-5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine
• 英文别名: 5-methyl-7-phenyl-1,7-dihydro-[1,2,4]triazolo[1,5-a]pyrimidin-2-amine
• CAS: 148612-47-9
• 化学式: C₁₂H₁₃N₅
• mdl: MFCD28246389
• 分子量: 227.269
• InChiKey: NWRJVONZNSBNJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  68.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  3,5-二氨基-1,2,4-三氮唑 、 苄叉丙酮 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 2-amino-5-methyl-7-phenyl-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidine
  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

• Partially hydrogenated 2-amino[1,2,4]triazolo[1,5-a]pyrimidines as synthons for the preparation of polycondensed heterocycles: reaction with chlorocarboxylic acid chlorides
  作者：Victor M. Chernyshev、Dmitry A. Pyatakov、Andrey N. Sokolov、Alexander V. Astakhov、Eugene S. Gladkov、Svetlana V. Shishkina、Oleg V. Shishkin

  DOI：10.1016/j.tet.2013.11.090

  日期：2014.1

  of partially hydrogenated [1,2,4]triazolo[1,5-a:4,3-a′]dipyrimidin-5-ones and pyrimido[2′,1′:3,4][1,2,4]triazolo[5,1-b]quinazolin-12-ones. It may be more convenient to prepare such compounds through one-pot processes. Some reactions of the synthesized chlorides of polycondensed heterocycles have been studied. Conditions have been found to effect the selective synthesis of free bases, oxidative aromatization

  部分氢化的2-氨基- [1,2,4]三唑并[1,5一]嘧啶和2-氨基- [1,2,4]三唑并[5,1- b ]喹唑啉与氯乙酸的氯化物反应，3-氯丙酸和4-氯丁酸在0–5°C下通过2-氨基的酰化反应生成酰胺。在DMF引线在80-90℃加热该相应的3-氯丙衍生物选择性在N-3分子内烷基化形成氯化物的部分氢化[1,2,4]三唑并[1,5一个：4,3-一个'] dipyrimidin -5-酮和嘧啶并[2'，1'：3,4] [1,2,4]三唑并[5,1- b] quinazolin-12-ones。通过一锅法制备此类化合物可能更方便。已经研究了缩合杂环的合成氯化物的一些反应。已经发现条件影响游离碱的选择性合成，二氢嘧啶循环的氧化芳构化或水解，以及嘧啶酮环的选择性水解裂解或消除。一些所得的化合物代表新的中离子杂环。
• ——
  作者：V. V. Lipson、S. M. Desenko、V. D. Orlov、O. V. Shishkin、M. G. Shirobokova、V. N. Chernenko、L. I. Zinov'eva

  DOI：10.1023/a:1017531803879

  日期：——
• Synthesis and pharmacological activity of N-pyrimidinylsuccinaminic acids and succinimides
  作者：S. M. Desenko、V. D. Orlov、V. V. Lipson、E. N. Ryndina、A. V. Chuvurin、A. A. Kirichenko、N. I. Gorbenko

  DOI：10.1007/bf02218988

  日期：1994.3
• 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.
• A new approach to synthesis of 2-sulfonylamino-1,2,4-triazolo[1,5-a]pyrimidines
  作者：V. M. Chernyshev、A. N. Sokolov、V. A. Taranushich

  DOI：10.1134/s1070427207100175

  日期：2007.10

  A procedure for synthesis of 2-sulfonylamino-1,2,4-triazolo[1,5-a]pyrimidines by sulfonylation of 2-amino-4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines, followed by oxidation of intermediate 2-sulfonylamino4,7-dihydro-1,2,4-triazolo[1,5-a]pyrimidines, was suggested.