New Sulfonamides Derived from Carvacrol: Compounds with High Antibacterial Activity against Resistant <i>Staphylococcus aureus</i> Strains

Abstract

Nine new sulfonamides derived from carvacrol were prepared through a reaction between 4-hydroxy-2-isopropyl-5-methyl benzene sulfonyl chloride with various amines in excellent yields (76% -92%). The sulfonamides were characterized using spectrometric and spectroscopic methods. Among these compounds, three derivatives showed excellent results in antibacterial activity against resistant S. aureus strains, with MIC values ranging from 3.9 to 62.50 ppm. The sulfonamide derivative of 4-methylaniline (SULF-1) had the best performance for all tested strains of bacteria (MIC = 3.9 to 15.62 ppm). Furthermore, the sulfonamide derivative of 4-fluoro aniline (SULF-3), which also presented promising results, was found to have a synergistic effect when combined with tetracycline and partial synergistic effect when combined with ampicillin, exhibiting an FIC index between 0.50 and 0.75. The sulfonamide derivative of 4-methylaniline had a synergistic effect in combination with erythromycin exhibiting an FIC index of 0.37. Carvacrol in association with the antibiotics tested did not have a synergistic effect.

Antioxidant Activity, Molecular Docking, Quantum Studies and In Vivo Antinociceptive Activity of Sulfonamides Derived From Carvacrol

“…The synthetic procedures for the sulfonamides S1–S5 ( Scheme 1 ), following a recently reported methodology ( de Oliveira et al, 2016 ), were performed in good yields (85–95%).…”

“…The synthesis sulfonamides S1–S5 , as already described in the literature ( de Oliveira et al, 2016 ) was performed in two steps: firstly, the synthesis of 4-hydroxy-2-isopropyl-5-methylbenzene-1-sulfonyl chloride (ChS) was performed, subsequently, the ChS was used in reactions with different amines ( Scheme 1 ). ChS was obtained from the reaction of carvacrol to six equivalents of chlorosulfonic acid.…”

Antibacterial Properties of Carvacrol against Antibiotic- Resistant Bacteria, Enteric Bacteria, and Oral Pathogens

“…The number of bacterial pathogens resistant to multiple antibacterial agents has dramatically increased in the last decade. Nowadays, multidrug-resistant bacteria are drawn attention to an emergent global disease and a major public health problem [1][2]. The antimicrobial resistance occurring in bacterial pathogens causes high morbidity and mortality [3].…”

Synthesis and PAMPA Permeability Assay of New Sulfonyl Hydrazone Derivatives

“…Sulfur is present in many classes of compounds of great interest in medicinal chemistry, for example thiosemicarbazones [1] [2], thioureas [3], thiazolidinones [4], sulfonamides [5] [6], among others. Sulfonamides have been known and studied in the scientific environment for a long time, due to their biological properties, in particular their antibacterial activity [7] [8] [9].…”