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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

1
, 1
, 2
, 2
, 3
 and 1,*
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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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