DOI: https://doi.org/10.55373/mjchem.v28i2.186

Keywords: Biological activities, 2(3H)-benzoxazolone, Green synthesis, sulfonamide, DFT Calculation, Molecular docking.

Abstract

Two sulfonamide derivatives of 2(3H)-benzoxazolone were synthesised using ultrasonic irradiation, by condensation of para-toluenesulfonyl chloride with 6-amino-2(3H)-benzoxazolone and 6-amino-3-methyl-2(3H)-benzoxazolone, in the presence of triethylamine and methylene chloride as solvent. This environmentally friendly synthesis method had short reaction times and gave excellent yields. Characterization of the products were performed using FT-IR, (¹H, ¹³C NMR) and GC-MS. These compounds were screened for their antimicrobial activity. Compound M2 exhibited the strongest antibacterial activity against both Gram-positive and Gram-negative bacteria. Compound M2 exhibited the highest DPPH radical-scavenging activity, with an IC₅₀ of 0.40 μg/mL. The molecular docking study against dihydropteroate synthase (PDB ID 3TZF) showed that both compounds exhibited favourable binding affinities and strong interactions with the enzyme. DFT analyses provided important insights into the chemical reactivity of the two compounds, including molecular electrostatic potential, Fukui indices, and global descriptors. Both compounds exhibited outstanding drug-like properties, with generally acceptable toxicity profiles.