Synthesis of β-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity

A series of β-amino carbonyl compounds containing coumarin ( 4a – h ) and benzofuran ( 6a – i ) moieties was synthesized by a three component Mannich reaction of 3-acetyl-2 H -chromen-2-one ( 1 ) or 1-(1-benzofuran-2-yl) ethanone ( 5 ) with p -substituted aromatic aldehydes ( 2a – g ) and aromatic amines ( 3a – b ) in the presence of cerric ammonium nitrate as a catalyst. The newly synthesized compounds were screened for antimicrobial and antioxidant activities. Compounds 4b , 4e , 4f , 6f , 6g , and 6i showed microbial inhibition with minimal inhibition concentration ranging between 0.040 and 0.500 mg/mL, compounds 4b , 4c , 6c , 6e, and 6i showed promising free radical scavenging activity and compounds 4b , 4f , 6c , 6d, and 6h showed good chelating ability with Fe 2+ ions. The synthesized compounds were studied for docking on the enzyme, glucosamine-6-phosphate synthase to predict the binding affinity and orientation at the active site of the receptor.