Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of <em>N</em>-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives

• Main Authors: Petronio Filgueiras de Athayde-Filho, Jose Maria Barbosa-Filho, Vivyanne dos Santos Falcão-Silva, Jose Pinto Siqueira-Junior, Bruno Freitas Lira, Cledualdo Soares de Oliveira
• Format: Article
• Language: English
• Published: MDPI AG 2012-05-01
• Series: Molecules
• Subjects: 1,3,4-oxadiazole; <em>N</em>-acylhydrazone; <em>Staphylococcus aureus</em> drug-likeness
• Online Access: http://www.mdpi.com/1420-3049/17/5/5095

Five new 1-(2-(5-nitrofuran-2-yl)-5-(aryl)-1,3,4-oxadiazol-3-(2<em>H</em>)-yl) ethanone compounds <strong>5a–e</strong> were synthesized by cyclization of <em>N</em>-acylhydrazones <strong>4a–e</strong> with acetic anhydride under reflux conditions. Their structures were fully characterized by IR, <sup>1</sup>H-NMR, and <sup>13</sup>C-NMR. Furthermore, evaluations of the antibacterial activity of the 1,3,4-oxadiazoles <strong>5a–e</strong> and <em>N</em>-acylhydrazones <strong>4a–e</strong> showed strong activity against several strains of <em>Staphylococcus aureus</em>, with MICs between 4 μg/mL to 32 μg/mL. <em>In silico</em> 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 <strong>4a</strong> and <strong>5d</strong>, have potential to be new drug candidates.