Synthesis, Spectroscopic Characterization, DFT Calculations and Preliminary Antifungal Activity of New Piperine Derivatives

• Published in: Journal of the Brazilian Chemical Society 2021-03, Vol.32 (3), p.490-502
• Main Authors: Souza Jr, Joselito, Martins, Evandro, Souza, Helivaldo, de Oliveira, Rafael, Alves, Francinara, Lima, Edeltrudes, Cordeiro, Laísa, Trindade, Emmely, Lira, Bruno, Rocha, Gerd, de Athayde-Filho, Petronio, Barbosa-Filho, José
• Format: Article
• Language: English
• Subjects: CHEMISTRY, MULTIDISCIPLINARY
• ISSN: 0103-5053; 1678-4790; 1678-4790
• DOI: 10.21577/0103-5053.20200203

Four new piperine derivatives, PC1-PC4, were synthesized, and their structures were fully characterized by infrared (IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopies. Quantum chemical calculations were performed using density functional theory (DFT) with the B3LYP-D3/6-31G(d,p) and 6-311+G(2d,p) basis sets. Electronic properties, such as the energy gap between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) and some global chemical reactivity descriptors, were evaluated to study the reactivity and stability of the compounds. 1H and 13C NMR chemical shifts were calculated by using the gauge-invariant atomic orbital (GIAO) method and compared with experimental values. In addition, the compounds were evaluated in an antifungal study against Candida, Trichophyton and Microsporum strains, and only PC4 showed 70% inhibition in ten tested strains, with a minimum inhibitory concentration (MIC) ranging from 1.23-2.46 μmol mL-1 and a minimum fungicide concentration (MFC) ranging from 9.84-19.68 μmol mL-1, and presented a fungistatic effect.