Synthesis, In Silico and In Vitro Evaluation of Antimicrobial and Toxicity Features of New 4-[(4-Chlorophenyl)sulfonyl]benzoic Acid Derivatives.
Theodora-Venera ApostolMariana Carmen ChifiriucConstantin DraghiciLaura-Ileana SoceaLuminita Gabriela MarutescuOctavian Tudorel OlaruGeorge Mihai NițulescuElena Mihaela PahontuGabriel SarametStefania-Felicia BarbuceanuPublished in: Molecules (Basel, Switzerland) (2021)
The multi-step synthesis, physico-chemical characterization, and biological activity of novel valine-derived compounds, i.e., N-acyl-α-amino acids, 1,3-oxazol-5(4H)-ones, N-acyl-α-amino ketones, and 1,3-oxazoles derivatives, bearing a 4-[(4-chlorophenyl)sulfonyl]phenyl moiety are reported here. The structures of the newly synthesized compounds were confirmed by spectral (UV-Vis, FT-IR, MS, 1H- and 13C-NMR) data and elemental analysis results, and their purity was determined by RP-HPLC. The new compounds were assessed for their antimicrobial activity and toxicity to aquatic crustacean Daphnia magna. Also, in silico studies regarding their potential mechanism of action and toxicity were performed. The antimicrobial evaluation revealed that the 2-{4-[(4-chlorophenyl)sulfonyl]benzamido}-3-methylbutanoic acid and the corresponding 1,3-oxazol-5(4H)-one exhibited antimicrobial activity against Gram-positive bacterial strains and the new 1,3-oxazole containing a phenyl group at 5-position against the C. albicans strain.
Keyphrases
- ms ms
- oxidative stress
- staphylococcus aureus
- mass spectrometry
- high resolution
- molecular docking
- oxide nanoparticles
- amino acid
- magnetic resonance
- escherichia coli
- optical coherence tomography
- multiple sclerosis
- risk assessment
- fatty acid
- gram negative
- electronic health record
- magnetic resonance imaging
- single cell
- multidrug resistant
- high performance liquid chromatography
- data analysis
- artificial intelligence
- deep learning