Synthesis and antituberculosis activity of novel 5-styryl-4-(hetero)aryl-pyrimidines via combination of the Pd-catalyzed Suzuki cross-coupling and SNH reactions |
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| Institution: | 1. Ural Research Institute for Phthisiopulmonology, 22 Parts’ezda, 50, Ekaterinburg 620039, Russia;2. I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskoy Str., 22, Ekaterinburg 620990, Russia;3. Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia;1. Centre of Advanced Studies, Department of Chemistry, University of Rajasthan, Jaipur 302004, India;2. Semiconductor and Polymer Science Laboratory, Department of Physics, University of Rajasthan, Jaipur, India;1. Department of Chemistry, School of Technology, GITAM University, Hyderabad 502102, Telangana, India;2. Department of Microbiology, Faculty of Medicine, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand;1. Department of Studies in Chemistry, Karnatak University, Dharwad 580003, India;2. Department of Physics, Yuvaraja''s College, University of Mysore, Mysore 570005, India;1. Institut de Chimie Organique et Analytique, Université d’Orléans, UMR CNRS 7311, rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France;2. Équipe de Chimie Bioorganique & Analytique, URAC 22, Université Hassan II Mohammedia-Casablanca, BP 146, 28800 Mohammedia, Morocco |
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| Abstract: | Combination of the Suzuki cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions proved to be a convenient method for the synthesis of 5-styryl-4-(hetero)aryl substituted pyrimidines from commercially available 5-bromopyrimidine. All intermediate 5-bromo-4-(hetero)aryl substituted pyrimidines and also the targeted 5-styryl-4-(hetero)arylpyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H37Rv, avium, terrae, and multi-drug-resistant strain isolated from tuberculosis patients in Ural region (Russia). It has been found that some of these compounds possess a low toxicity and have a bacteriostatic effect, comparable and even higher with that of first-line antituberculosis drugs. |
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| Keywords: | Pyrimidine Antimicobacterial Tuberculosis Cross-coupling Nucleophilic aromatic substitution of hydrogen |
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