Unexpected synthesis of novel 2-pyrone derivatives: crystal structures, Hirshfeld surface analysis and computational studies

Here we report synthesis of three new compounds namely, 1-acetyl-1H-benzimidazolo-2(3H)-one (I), N-(5-acetyl-6-methyl-2-oxo-2H-pyran-4-yl)-N-(2-acetamidophenyl)acetamide (II) and N-(2-acetamidophenyl)-N-2-oxo-2H-pyran-4-yl)acetamide (III) have been synthesized and characterized by single crystal X-ray diffraction. Compounds I and II crystallize in the monoclinic space groups P21/n, and P21/c, respectively, while III crystallizes in the triclinic space group P-1. The theoretical parameters of I–III have been calculated through density functional theory (DFT) by using the hybrid functional B3LYP and basis set 6-311++G**. These theoretical parameters have been compared with the experimental ones obtained by XRD. The significant intermolecular interactions arising in crystal packing are rationalized by means of the Hirshfeld surface analysis method. The major intermolecular contacts in the Hirshfeld surfaces of I–III are from H…H contacts. In addition, binding modes of I–III within Tyrosine-protein kinase JAK2 were investigated using molecular docking and molecular dynamics simulation studies. Communicated by Ramaswamy H. Sarma. © 2020, © 2020 Informa UK Limited, trading as Taylor & Francis Group.

Sebhaoui J.1 , El Bakri Y. , Lai C.-H.3, 4 , Karthikeyan S. 5 , Anouar E.H.6 , Mague J.T.7 , Essassi E.M.1
Taylor and Francis Ltd.
  • 1 Laboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des Médicaments, Pôle de Compétences Pharmacochimie, URAC 21, Faculté des Sciences, Mohammed V University Rabat, Rabat, Morocco
  • 2 South Ural State University, Chelyabinsk, Russian Federation
  • 3 Department of Medical Applied Chemistry, Chung Shan Medical University, Taichung, Taiwan
  • 4 Department of Medical Education, Chung Shan Medical University Hospital, Taichung, Taiwan
  • 5 Organic Chemistry Department, Science Faculty, RUDN University, Moscow, Russian Federation
  • 6 Department of Chemistry, College of Science and Humanities in Al-Kharj, Prince Sattam bin Abdulaziz University, Al-Kharj, Saudi Arabia
  • 7 Department of Chemistry, Tulane University, New Orleans, LA, United States
Ключевые слова
benzimidazole; crystal structure; DFT calculations; molecular docking; molecular dynamics simulation; Pyrane
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