A series of new pyrrole-coupled carboxamide derivatives had been synthesized and amply characterized by various techniques, viz FTIR, 1H-NMR, 13C-NMR, and LCMS. All these compounds had undergone evaluation for their PASS, BBB, pharmacophore model, ADME, and bioactive score. The antibacterial properties of all the derivatives were examined and compound 5i demonstrated strong antibacterial activity against MRSA. A membrane damage investigation supported by SEM pictures, cellular content leakage, potassium efflux, and bacterial respiration suppression showed that compound 5i had anti-MRSA properties. A good binding score of -9.11 was found for compound 5i against the MRSA protein 6FTB in an in silico molecular docking analysis, compared to a score of -10.25 for streptomycin. Based on these findings, compound 5i can be further studied in order to develop it as a drug to treat MRSA infections.