title: Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-acylhydrazones and new 1,3,4-oxadiazole derivatives.
abstract: Five new 1-(2-(5-nitrofuran-2-yl)-5-(aryl)-1,3,4-oxadiazol-3-(2H)-yl) ethanone compounds 5a-e were synthesized by cyclization of N-acylhydrazones 4a-e with acetic anhydride under reflux conditions. Their structures were fully characterized by IR, ¹H-NMR, and ¹³C-NMR. Furthermore, evaluations of the antibacterial activity of the 1,3,4-oxadiazoles 5a-e and N-acylhydrazones 4a-e showed strong activity against several strains of Staphylococcus aureus, with MICs between 4 μg/mL to 32 μg/mL. In silico studies of the parameters of Lipinski's Rule of Five, as well as the topological polar surface area (TPSA), absorption percentage (% ABS), drug likeness and drug score indicate that these compounds, especially 4a and 5d, have potential to be new drug candidates.
authors.affiliation: Department of Chemistry, Federal University of Paraiba, João Pessoa, PB 58059-900, Brazil.
authors.forename: Cledualdo Soares
authors.initials: CS
authors.lastname: de Oliveira
authors.forename: Bruno Freitas
authors.initials: BF
authors.lastname: Lira
authors.forename: Vivyanne
authors.initials: V
authors.lastname: dos Santos Falcão-Silva
authors.forename: Jose Pinto
authors.initials: JP
authors.lastname: Siqueira
authors.forename: Jose Maria
authors.initials: JM
authors.lastname: Barbosa-Filho
authors.forename: Petronio Filgueiras
authors.initials: PF
authors.lastname: de Athayde-Filho
mesh_terms: D000089:Acetic Anhydrides / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003198:Computer Simulation; D024901:Drug Resistance, Multiple, Bacterial; D006835:Hydrazones / Q000138:chemical synthesis* / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects* / Q000254:growth & development; D013499:Surface Properties
chemical_list: D000089:Acetic Anhydrides; D000900:Anti-Bacterial Agents; D006835:Hydrazones; D010069:Oxadiazoles; C031800:acetic anhydride