One‐Pot Synthesis of Novel 3‐{(1H‐Benzo[d]Imidazol‐2‐yl)Amino(Phenyl)Methyl}Benzofuran‐2(3H)‐Ones as Antimicrobial Agents and Their Molecular Docking Studies

Aminobenzimidazole‐coumaranone conjugates, specifically 3‐{[(1 H ‐benzo[ d ]imidazol‐2‐yl)amino](substitutedphenyl)methyl}benzofuran‐2(3 H )‐ones, were synthesized through a one‐pot reaction involving 2‐coumaranone, aryl aldehydes, and 2‐aminobenzimidazole. This reaction, catalyzed by triethylamine in acetonitrile at 80°C, achieved yields of up to 85%. Preparative liquid chromatography successfully isolated compounds 4b and 4c as two isomers with purities reaching 99.30%. Their absolute configurations, ( S , R ) for compound 4b and ( R , S ) for compound 4c , were determined using electronic circular dichroism and confirmed via TD‐DFT calculations. The antimicrobial potential of the synthesized compounds ( 4a–j ) and their enantiopure isomers ( 4b′ , 4b″ , 4c′ , 4c″ ) was evaluated against the bacterial strains Bacillus subtilis , Staphylococcus aureus , Staphylococcus proteolyticus , and the fungal strains Candida albicans and Aspergillus niger . Notably, compounds 4a , 4d , 4i , and 4j exhibited superior antimicrobial activity. Molecular docking studies further reinforced these results, revealing strong receptor binding affinities (−7.5 to −10.5 kcal/mol), which surpass those of standard drugs. These findings highlight the promising potential of aminobenzimidazole‐coumaranone conjugates as effective antimicrobial agents.