Antiparasite and antimycobacterial activity of passifloricin analogues

Abstract Several structural analogues of the polyketide passifloricin lactone were synthesized using asymmetric stereoselective allylations and ring-closing methateses as key reactions. These compounds were active in vitro against intracellular amastigotes of Leishmania panamensis (strain UA140), trophozoites of Plasmodium falciparum (strain NF54), and Mycobacterium tuberculosis (strain H 37 Rv). However, in spite of the significative antiparasitic activity of some synthetic analogues a high cytotoxicity was also observed. Based on these results a lactam derivative was also synthesized. This compound maintained a good level of activity with less toxicity.