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

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

1
Department of Chemistry, Federal University of Paraiba, João Pessoa, PB 58059-900, Brazil
2
Department of Molecular Biology, Federal University of Paraíba, João Pessoa, PB 58059-900, Brazil
3
Laboratory of Pharmaceutical Technology, Federal University of Paraíba, João Pessoa, PB 58051-900, Brazil
*
Author to whom correspondence should be addressed.
Received: 19 March 2012 / Revised: 18 April 2012 / Accepted: 19 April 2012 / Published: 3 May 2012
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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 1,3,4-oxadiazole; N-acylhydrazone; Staphylococcus aureus; drug-likeness
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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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.

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