Synthesis, molecular properties prediction, and anti-staphylococcal activity of N-acylhydrazones and new 1,3,4-oxadiazole derivatives.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Cledualdo Soares de OliveiraPetrônio Filgueiras de Athayde-Filho

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.

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Citations

Mar 25, 2014·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Raied M ShakirMahmood Ameen Abdulla
Aug 29, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Cledualdo Soares de OliveiraPetrônio Filgueiras de Athayde-Filho
May 8, 2015·Biological & Pharmaceutical Bulletin·Nadia Abdalla KhalilSoha Hussein Emam
Oct 17, 2018·Mini Reviews in Medicinal Chemistry·Garima VermaMohammad Shaquiquzzaman
Aug 5, 2020·Current Organic Synthesis·Mohamed Ahmed Elian Sophy, Mohamed Ahmed Mahmoud Abdel Reheim
Aug 28, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rubina MunirMuhammad Makshoof Athar

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