Synthesis of febrifuginol analogues and evaluation of their biological activities

Abstract A new series of febrifuginol analogues was prepared from l -glutamic acid. An antimalarial activity evaluation against chloroquine-sensitive (T96) and chloroquine-resistant (K1) Plasmodium falciparum indicated that all the tested compounds had very strong inhibitory activity. Compounds 4 and 17b ′ were inactive against KB, MCF7, HepG2 and LU1 cell lines even at a concentration of 100 μM, while they exhibited significant inhibition towards P. falciparum . Comparison of the antimalarial activity and the cytotoxic properties revealed that the 2′ S isomers were more active than the corresponding 2′ R isomers for this series of febrifuginol analogues, indicating that the C-2′ position is critical for the biological activity of this class of compounds.