Biological Activity Evaluation of Some New Benzenesulphonamide Derivatives

Abstract

Bacterial resistance to antibiotics has become one of the most challenging problems of infectious disease treatment. Ten new derivatives of benzenesulphonamide bearing carboxamide functionality were synthesized and investigated for their in vivo anti-inflammatory, in vitro anti-microbial and anti-oxidant activities. The base promoted reactions of the appropriate amino acids with substituted benzenesulphonyl chlorides gave the benzene sulphonamides (3a-j) in excellent yields. Palladium mediated amidation of the benzenesulphonamides (3a-j) and butylamine gave the new carboxamides (4a-j) in excellent yield. Compounds 4a and 4c inhibited carrageenan induced rat-paw edema at 94.69, 89.66, and 87.83% each at 1, 2, and 3 h, respectively. In the antimicrobial activity, compound 4d (MIC 6.72 mg/mL) was most potent against E. coli, compound 4h (MIC 6.63 mg/mL) was the most active against S. aureus, compound 4a (MIC 6.67 and 6.45 mg/mL) was most active against P. aeruginosa and S. typhi, respectively, compound 4f (MIC 6.63 mg/mL) was the most active against B. subtilis, compounds 4e and 4h (MIC 6.63 mg/mL) each were the most active against C. albicans, while compound 4e (MIC 6.28 mg/mL) was most active against A. niger. Only compound 4e (IC50 0.3287 mg/mL) had comparable activity with Vitamin C (IC50 0.2090 mg/mL).

Antioxidant Activities of a New Chemotype of Piper cubeba L. Fruit Essential Oil (Methyleugenol/Eugenol): In Silico Molecular Docking and ADMET Studies

“…As shown, numerous interactions between human peroxiredoxin 5-selected phytocompounds are close to the active site of the enzyme. Our finding also corroborates perfectly those of Eze et al [ 54 ], demonstrating that the docked 1-(Phenylsulphonyl)-N-propylpyrrolidine-2-carboxamide with human peroxiredoxin 5 exhibited higher binding energy (−13.86 kcal mol −1 ), creating interactions with Thr44, Pro40, Pro 45, Gly46, Arg127, Thr147, and Cys47 residues. Additionally, with the same therapeutic target, caryophyllene oxide (−7.2 kcal/mol) from Cymbopogon citratus essential oil established non-covalent interactions with Pro 40, Thr 147, Thr 44, Phe 120, Pro 45, Leu 116, and Ile 119, sharing a large number of common residues with the active site of the investigated enzyme.…”

HR-LCMS-Based Metabolite Profiling, Antioxidant, and Anticancer Properties of Teucrium polium L. Methanolic Extract: Computational and In Vitro Study

“…Our molecular docking results with antioxidant human peroxiredoxin 5 were perfectly correlated with those of Eze et al [105], confirming the same and highest binding pose of 1-(phenylsulphonyl)-N-propylpyrrolidine-2-carboxamide in the binding cavity of human peroxiredoxin 5 with a binding energy of (−13.86 kcal mol −1 ) and interactions with THR44, PRO40, PRO 45, GLY46, ARG127, THR147, and CYS A47 residues. Similarly, α-tocopherol (−7.2 kcal mol −1 ) Cymbopogon citratus essential oil was perfectly fitted into the cavity of peroxiredoxin 5 establishing H-bonding with Arg 127(A) and non-covalent interactions with ASP A113, THR A147, LEU A116, SER A115, LEU A112, PRO A40, THR A44, GLY A46, CYS A47, PHE A120, and ASP A145.…”

New chalcone derivatives as potential antimicrobial and antioxidant agent

“…The mechanism of resistance is usually encoded genetically and as such can be transferable 1 . This wide increase in resistance mechanism negatively affects the therapeutic efficacy of a whole class of drugs 2 .…”