Efficient synthesis of 16 aromatic Morita–Baylis–Hillman adducts: Biological evaluation on Leishmania amazonensis and Leishmania chagasi

Sixteen aromatic Morita–Baylis–Hillman adducts (MBHA) 1–16 were efficiently synthesized in a one step Morita–Baylis–Hillman reaction (MBHR) involving commercial aldehydes with methyl acrylate or acrylonitrile (81–100% yields) without the formation of side products on DABCO catalysis and at low temperature (0 °C). The toxicities of these compounds were assessed against promastigote form of Leishmania amazonensis and Leishmania chagasi. The low synthetic cost of these MBHA, green synthetic protocols, easy one-step synthesis from commercially available and cheap reagents as well as the very good antileishmanial activity obtained for 14 and 16 (IC50 values of 6.88 μg mL−1 and 11.06 μg mL−1 respectively on L. amazonensis; 9.58 μg mL−1 and 14.34 μg mL−1 respectively on L. chagasi) indicates that these MBHA can be a novel and promising class of anti-parasitic compounds.

We described “one-pot” Morita-Baylis-Hillman reactions to produced 16 aromatic compounds (81-100%), its bio-evaluations on L. Amazonensis and L. chagasi and a relationship between the chemical structure and biological activity (S.A.R.).Figure optionsDownload as PowerPoint slide