Diastereoselective Synthesis of Potent Antimalarial -β-lactam Agents.

Fifteen novel β-lactams bearing N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2- aminoethyl) β-lactams were synthesized by [2+2] ketene-imine cycloaddition reaction (Staudinger). The cycloaddition reaction was found to be totally diastereoselective leading exclusively to theformation of -β-lactam derivatives. These newly synthesized β-lactams were evaluated for their antimalarial activity against K14 resistant strain and showed good to excellent EC50 values. Of the thirty β-lactams tested, and showed IC50 < 20 µM while , , , , , , , , and exhibited IC50 <50 . Compounds 5c, 5h, and 5q-t were examined for their anticancer properties against K562 cell line and 5s showed the best activity. Compounds , , , were tested against , and showed no activity below 125 µg/mL.