Structural characterization, DFT calculations, ADMET studies, antibiotic potentiating activity, evaluation of efflux pump inhibition and molecular docking of heterocylcic chalcone (E)-1-(4-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one

Abstract

Chalcones are compounds with biological activities in different beings. They have a simple and easy to handle structure due to the α-β-unsaturated bridge responsible for most biological activities. They are facilitating the synthesis of compounds that are more effective in combating severe bacterial infections and other pathologies that, together with known antibiotics, can potentiate their action. This work's objective was to study chalcone (E)-1-(4-aminophenyl)-3-(thiophen-2-yl)prop‑2-en-1-one (C13H11NOS) by single-crystal X-ray Diffraction (XRD), Fourier Transform Raman (FT-Raman), Attenuated Total Reflection Fourier Transform Infrared (ATR-FTIR), and Ultraviolet-visible (UV–Vis) spectroscopy. Theoretical quantum chemistry calculations were performed to obtain information about their chemical and physical properties. In vitro assays of antibacterial activity, and efflux pump and in silico study by docking molecular were carried out. The pharmacokinetic properties were predicted by metabolism, excretion, and toxicity (ADMET). These results indicate that chalcone can modulate the resistance of strains SA1199B and K2068 to the fluoroquinolones Norfloxacin and Ciprofloxacin, probably through inhibition of the NorA and MepA pumps respectively.