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

Cledualdo Soares de Oliveira 1 email, Bruno Freitas Lira 1 email, Vivyanne dos Santos Falcão-Silva 2 email, Jose Pinto Siqueira-Junior 2 email, Jose Maria Barbosa-Filho 3 email and Petronio Filgueiras de Athayde-Filho 1,* email
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; in revised form: 18 April 2012 / Accepted: 19 April 2012 / Published: 3 May 2012
PDF Full-text Download PDF Full-Text [194 KB, uploaded 3 May 2012 10:00 CEST]
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

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert