Synthesis, Structural Analysis and Antibacterial Properties of a Novel β‐Aminoenone

Abstract

(Z)-3-butylamino-4,4,4-trifluoro-1-(2-hydroxyphenyl)but-2-en-1-one (1), a new β-aminoenone, has been investigated in terms of its intra- and intermolecular interactions. Vibrational, electronic and nuclear magnetic resonance spectroscopies were used for the characterization,while X-ray diffraction methods afforded the determination of the crystal structure. The compound is arranged in the crystal lattice as centre-symmetric H-bonded dimeric aggregates (C2/c monoclinic space group). Both experimental (infrared, Raman, ultraviolet-visible transitions and X-ray diffraction data) and theoretical (Quantum Theory of Atoms in Molecules and Natural Bond Orbital approaches, calculated spectra and conformational analysis) methods were used to obtain a deep insight into the intra- and intermolecular contacts. The interactions were quali- and quantitatively analysed and the data compared with closely related compounds. In vitro experiments were carried out in this work to evaluate the antibacterial activity of 1 against Gram-positive and Gram-negative bacteria, particularly Pseudomonas aeruginosa (ATCC 27853) and Staphylococcus aureus (6538).Compound 1 demonstrated a discernible suppression of biofilm formation and quorum sensing of both bacterial strains, indicating that it may be developed as an antibacterial candidate to reduce bacterial resistance and persistence on surfaces across a range of industries.