RESUMO
This review provides readers with an overview of the main synthetic methodologies for 1,3,4-oxadiazole derivatives, and of their broad spectrum of pharmacological activities as reported over the past twelve years.
Assuntos
Oxidiazóis/síntese química , Oxidiazóis/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Antibacterianos/farmacologia , Anti-Inflamatórios não Esteroides/síntese química , Anti-Inflamatórios não Esteroides/química , Anti-Inflamatórios não Esteroides/farmacologia , Antifúngicos/síntese química , Antifúngicos/química , Antifúngicos/farmacologia , Oxidiazóis/química , Pirrolidinas/química , Pirrolidinas/farmacologia , Pirrolidinas/uso terapêutico , Pirrolidinonas/química , Pirrolidinonas/farmacologia , Pirrolidinonas/uso terapêutico , Raltegravir PotássicoRESUMO
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.
Assuntos
Antibacterianos/síntese química , Hidrazonas/síntese química , Oxidiazóis/síntese química , Staphylococcus aureus/efeitos dos fármacos , Anidridos Acéticos/química , Antibacterianos/farmacologia , Simulação por Computador , Farmacorresistência Bacteriana Múltipla , Hidrazonas/farmacologia , Interações Hidrofóbicas e Hidrofílicas , Espectroscopia de Ressonância Magnética , Testes de Sensibilidade Microbiana , Modelos Moleculares , Oxidiazóis/farmacologia , Staphylococcus aureus/crescimento & desenvolvimento , Propriedades de SuperfícieRESUMO
Two salts of the mesoionic compounds 1,4-diphenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-thiol chloride (MC-1) and 4-phenyl-5-(5-nitro-2-furanyl)-1,3,4-thiadiazolium-2-phenylamine chloride (MC-2) were synthesized utilizing 1,4-diphenyl-thiosemicarbazide and 5-nitro-2-furoyl chloride as starting materials. Their structures were characterized by IR, ¹H-NMR, ¹³C-NMR and elemental analysis. These compounds were analyzed for their influence on the effectiveness of norfloxacin, tetracycline, and erythromycin (standard antibiotics) against resistant strains of Staphylococcus aureus. MC-1 and MC-2, at sub-inhibitory concentrations of 16 µg/mL, favourably modulated the antibiotic activity of tetracycline by 16- and 32-fold, respectively (MIC), and that of erythromycin by 4-fold.
