1. Structural and spectroscopic analysis and evaluation of cytotoxic activity of 2-hydroxychalcones against human cancer cell lines
- Author
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Cláudia Pessoa, Priscila Teixeira da Silva, Murilo S. S. Julião, Alexandre Magno Rodrigues Teixeira, Aldeneide Soares de Paiva, Francisco Washington Araújo Barros-Nepomuceno, A. C. H. Barreto, Daniel Pascoalino Pinheiro, Paulo Nogueira Bandeira, Pedro de Lima-Neto, Antonio Linkoln Alves Borges Leal, Francisco W.Q. Almeida-Neto, Hélcio Silva dos Santos, and Emmanuel Silva Marinho
- Subjects
Chalcone ,Organic Chemistry ,Carbon-13 NMR ,Quantum chemistry ,Analytical Chemistry ,Inorganic Chemistry ,chemistry.chemical_compound ,Ultraviolet visible spectroscopy ,chemistry ,Computational chemistry ,Proton NMR ,Molecular orbital ,Reactivity (chemistry) ,Spectroscopy - Abstract
Chalcones and their derivatives exhibit a broad spectrum of pharmacological activities, including antiproliferative activities. Accordingly, they are deemed robust anticancer candidates for cytotoxicity assays. Herein, we synthesized and characterized four chalcones using nuclear magnetic resonance (1H NMR and 13C NMR), Fourier transform Raman (FT-Raman), attenuated total reflection Fourier transform infrared (ATR-FTIR), and ultraviolet-visible (UV–vis) spectroscopy. Theoretical calculations of quantum chemistry were performed to obtain data regarding normal vibration modes, frontier molecular orbitals, molecular electrostatic potential maps, theoretical UV–vis spectra, and quantum chemical parameters expected for these chalcones. In addition, we evaluated the cytotoxic potential of these compounds. For synthesized compounds, quantum chemical calculations demonstrated excellent correlation with experimental data. The electronic properties revealed that chalcones 1 and 4 possess a higher electrophilic character, while chalcones 2 and 3 possess a higher nucleophilic character. Chalcone 3 demonstrated the highest value of HOMO energy, indicating the greatest propensity to donate electronic density among the four compounds. According to the HOMO-LUMO energy gap and global hardness, the reactivity of chalcones should follow the order 1
- Published
- 2021