A newly synthesized 6-methyl-7H,8H,9H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8-one for potential inhibitor of adenosine A1 receptor: a combined experimental and computational studies

6-Methyl-7H,8H,9H-[1,2,4]triazolo[4,3-b][1,2,4]triazepin-8-onehas been synthesized, characterized by spectroscopic techniques (FT-IR, 1H and 13C NMR) and finally the structure was confirmed by single crystal X-ray diffraction studies. In the title molecule, C6H7N5O, the 7-membered ring adopts a bowl-like conformation. In the crystal, the molecules form stacks along the c-axis direction through offset π-stacking interactions between the 5-membered rings and C–H···N hydrogen bonds. The stacks are associated via a combination of N–H···N, C–H···O and C–H···N hydrogen bonds. Further, the Hirshfeld surface analysis reveals the nature of molecular interactions and the fingerprint plot provides information about the percentage contribution from each individual molecular contact to the surface. In addition, due to its biological interest the target molecule adenosine A1 receptor was found based on Structural Activity Relationship (SAR) analysis and, further, subjected into molecular docking and molecular dynamics analysis to understand the binding interaction and stability of the molecule in adenosine A1 receptor system. Furthermore, the Density Functional Theory (DFT) calculations were carried for free compound and the compound in active site (single point DFT), to know the internal stability. Communicated by Ramaswamy H. Sarma. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.

El Bakri Y. , Karthikeyan S. 2 , Anouar E.H.3 , Sebhaoui J.1 , Ben Ali A. , El Ghayati L. , Essassi E.M.1 , Mague J.T.5
Taylor and Francis Ltd.
  • 1 Laboratoire de Chimie Organique Heterocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Faculte des Sciences, Universite Mohammed V, Rabat, Morocco
  • 2 Organic Chemistry Department, Science Faculty, RUDN University, Moscow, Russian Federation
  • 3 Department of Chemistry, College of Science and Humanities, Prince Sattam bin Abdulaziz University, Al Kharj, Saudi Arabia
  • 4 Laboratoire de Chimie Appliquée des Matériaux, Centres des Sciences des Matériaux, Faculty of Sciences, Mohammed V University in Rabat, Rabat, Morocco
  • 5 Department of Chemistry, Tulane University, New Orleans, LA, United States
Ключевые слова
1,2,4-Triazole[4,3-b][1,2,4]triazepine; crystal structure; DFT calculations; Hirshfeld surface analysis; molecular docking; molecular dynamics simulation
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