Synthesis, photostability and antibacterial activity of a series of symmetrical α,β-unsaturated ketones as potential UV filters

Abstract

A series of three symmetrical α,β-unsaturated ketones, namely, (1E,4E)-1,5-bis[4-(methylthio)phenyl]penta-1,4-dien-3-one, 1, (1E,4E)-1,5-bis[4-(dimethylamino)phenyl]penta-1,4-dien-3-one, 2, and (1E,4E)-1,5-bis[4-(ethyl)phenyl] penta-1,4-dien-3-one, 3, were synthesized in excellent yields (above 70%) and within a short reaction time (1 h), via an improved Knoevenagel condensation with acetyl acetone and substituted benzaldehydes. All the compounds were fully characterized by UV/Vis, IR, NMR and mass spectrometry. In addition, compound 1 was characterized by single crystal X-ray diffraction. The photostability of the prepared compounds was investigated in solvents of different polarity and proticity by exposure to simulated solar radiation. Three solvents were used, namely, ethyl acetate, dimethylsulfoxide and methanol. The change in UV absorption was monitored by a standard spectrophotometric method and photodegradation products were identified by 1H NMR. According to the results, 1 and 3 were not photostable, and suffered significant changes in their UV absorption spectra. Compound 2, on the other hand, was observed to be considerably photostable in the polar protic solvent methanol but less photostable in the polar aprotic solvent dimethylsulfoxide. All three compounds (1–3) photodegraded appreciably in the less polar aprotic solvent ethyl acetate. Therefore, their photostability is solvent dependent. The antibacterial activity of 1–3 was evaluated by means of the modified broth microdilution method against both gram-negative and gram-positive bacterial strains. Compounds 2 (methylated amine) and 3 (ethyl) have electron-releasing substituents and they were found to have excellent activity against all the tested bacteria. Thus, compounds 2 and 3 can be further explored as potential leads for the development of cheaper, safer, more effective and potent antibiotics against both gram-positive and gram-negative bacterial strains, and compound 2 is a good candidate for use in sunscreen formulations if dissolved in a polar solvent.