7362-71-2Relevant academic research and scientific papers
Synthesis and in vitro anti Leishmania amazonensis biological screening of Morita-Baylis-Hillman adducts prepared from eugenol, thymol and carvacrol
Seixas Xavier, Francisco José,Da Franca Rodrigues, Klinger Antonio,De Oliveira, Ramon Guerra,Lima, Claudio Gabriel,Da Camara Rocha, Juliana,Keesen, Tatjana Souza Lima,De Oliveira, Marcia Rosa,Silva, Fábio Pedrosa Lins,De Almeida Vasconcellos, Mário Luiz Araújo
, (2016)
Leishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation against promastigotes of Leishmania amazonensis. The new MBHAs are prepared in two steps from essential oils in moderate to good yields and present IC50 values in the range of 22.30-4.71 μM. Moreover, the selectivity index to the most potent compound is very high (SIrb > 84.92), far better than that of Glucantime (SIrb 1.39) and amphotericin B (SIrb = 22.34). Conformational analysis were carried out at the M062X//6-31+G(d,p) level of theory to corroborate a hypothesis about the nitroaromatic bioreduction mechanism.
