N-(4-bromophenyl)furan-2-carboxamide (3) was synthesized by the reaction furan-2-carbonyl chloride (1) and 4-bromoaniline (2) in the presence of Et3N in excellent yields of 94%. The carboxamide (3) was arylated by employing triphenylphosphine palladium as a catalyst and K3PO4 as a base to afford N-(4-bromophenyl)furan-2-carboxamide analogues (5a-i) in moderate to good yields (43–83%). Furthermore, we investigated the in vitro anti-bacterial activities of the respective compounds against clinically isolated drug-resistant bacteria A. baumannii, K. pneumoniae, E. cloacae and S. aureus. The molecule (3) was found to be the most effective activity against these bacteria, particularly NDM-positive bacteria A. baumannii as compared to various commercially available drugs. Docking studies and MD simulations further validated it, expressing the active site and molecular interaction stability.

The (S)-4-bromo-N-(1-phenylethyl)benzamide (3) was synthesized in excellent yield (93 %) by the reaction of 4-bromobenzoic acid (1) and (S)-1-phenylethanamine (2) with the coupling reagent titanium tetrachloride (TiCl 4 ). Further, the Pd(0) catalyst was employed to form (S)-4-bromo-N-(1phenylethyl)benzamide analogues (5 a-i) by reacting various aryl boronic acids with 4-bromo-N-(1-phenylethyl)benzamide (3) in moderate to good yields (62-89 %). Furthermore, DFT studies were carried out to compute optimized geometries, frontier molecular orbitals, polarizability (α), hyperpolarizability (β), MESP, reactivity descriptors, and NMR spectra. The measured NMR values matched the experimental NMR values well. In this series (5 a-i), we predicted that the highest energy difference between the HOMO-LUMO of compound (5 a) has 4.98 eV, resulting in a more stable compound, and compound (5 g) has the lowest energy difference between the HOMO-LUMO 4.63 eV, resulting in the least stable compound. Compound (5h) has the highest hyperpolarizability (β) value, exhibits a better non-linear optical (NLO) behaviour compared as compare to other synthesized compounds in the series.