Synthesis and antimicrobial activity of highly functionalised novel β-lactam grafted spiropyrrolidines and pyrrolizidines

A facile and one-pot synthesis of a series of novel spiropyrrolidines/pyrrolizidines with β-lactam substituent has been accomplished through 1,3-dipolar cycloaddition reaction of alkenyl esters derived from β-lactam aldehyde as dipolarophile with the dipole azomethine ylide derived from 1,2- and 1,3-diketones and secondary amino acids. The synthesized compounds were evaluated for antimicrobial activities and found to exhibit relatively good antibacterial activity at lower concentration against four human bacterial pathogens.

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► A series of β-lactam fused spiropyrrolidineds was synthesized by 1,3-dipolar cycloaddition reaction.
► The compounds were found to have antibacterial activity against selected pathogens.
► Some of the compounds were found to have better activity than the reference compound tetracycline.
► The grafting of β-lactam with pyrrolidine unit has enhanced the overall bioactivity of the products.