Author/Authors :
Jarrahpour, Aliasghar Department of Chemistry - College of Sciences - Shiraz University, Shiraz, Iran , Rostami, Maryam Department of Chemistry - College of Sciences - Shiraz University, Shiraz, Iran , Eacute, V Faculté de pharmacie - Physiopathologie & Pharmacologie - AixMarseille Université, Marseille, France , Sinou, Ronique Aix-Marseille Université , Latour, Christine Djouhri Centre de Recherche en Cancérologie de Marseille (CRCM), -Institut Paoli Calmettes, Marseille, France , Boukta, Lamia Centre de Recherche en Cancérologie de Marseille (CRCM), -Institut Paoli Calmettes, Marseille, France , Brunel, Jean Michel Centre de Recherche en Cancérologie de Marseille (CRCM), -Institut Paoli Calmettes, Marseille, France
Abstract :
Fifteen novel β-lactams bearing N-ethyl tert-butyl carbamate group 5a-o and fifteen N-(2-
aminoethyl) β-lactams 6a-o were synthesized by [2+2] ketene-imine cycloaddition reaction
(Staudinger). The cycloaddition reaction was found to be totally diastereoselective leading
exclusively to theformation of cis-β-lactam derivatives. These newly synthesized β-lactams
were evaluated for their antimalarial activity against p. falciparum K14 resistant strain and
showed good to excellent EC50 values. Of the thirty β-lactams tested, 5 h, 6a and 6c showed
IC50 < 20 μM while 5b, 5c, 5e, 5f, 5g, 5i, 5j, 6d, 6g and 6h exhibited IC50 <50 . Compounds
5c, 5h, and 5q-t were examined for their anticancer properties against K562 Leukemia cell line
and 5s showed the best activity. Compounds 3a-j, 5a-o, 6a-o, were tested against S. aureus ,
E. coli, C. albicans and showed no activity below 125 μg/mL.
Keywords :
Antimalarial activity , Staudinger , P. falciparum , 2-Azetidinones , tert-butyl carbamate , N -(2-aminoethyl) β-lactams
