Molecules 2012, 17(5), 5095-5107; doi:10.3390/molecules17055095
Article

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

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Received: 19 March 2012; in revised form: 18 April 2012 / Accepted: 19 April 2012 / Published: 3 May 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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.
Keywords: 1,3,4-oxadiazole; N-acylhydrazone; Staphylococcus aureus; drug-likeness
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MDPI and ACS Style

de Oliveira, C.S.; Lira, B.F.; dos Santos Falcão-Silva, V.; Siqueira-Junior, J.P.; Barbosa-Filho, J.M.; de Athayde-Filho, P.F. Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives. Molecules 2012, 17, 5095-5107.

AMA Style

de Oliveira CS, Lira BF, dos Santos Falcão-Silva V, Siqueira-Junior JP, Barbosa-Filho JM, de Athayde-Filho PF. Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives. Molecules. 2012; 17(5):5095-5107.

Chicago/Turabian Style

de Oliveira, Cledualdo Soares; Lira, Bruno Freitas; dos Santos Falcão-Silva, Vivyanne; Siqueira-Junior, Jose Pinto; Barbosa-Filho, Jose Maria; de Athayde-Filho, Petronio Filgueiras. 2012. "Synthesis, Molecular Properties Prediction, and Anti-staphylococcal Activity of N-Acylhydrazones and New 1,3,4-Oxadiazole Derivatives." Molecules 17, no. 5: 5095-5107.

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