Resumen de Síntesis y Actividad Antimalárica de Estirilquinolinas sobre Plasmodium falciparum.

Gilmar Santafe Patiño, Emy L. Sanchez, Omar L. Torres

• español

  Con el propósito de encontrar nuevas moléculas activas sobre la malaria, se sintetizaron las estirilquinolinas 2-[(E)-2-(2-metoxifenil)etenil]quinolina (1), 2-[(E)-2-(2-clorofenil)etenil]quinolina (2) y 2-[(£)-2-(4-isopropilfenil) etenil] quinolina (3) a partir de la reacción de condensación tipo Perkin entre quinaldina y aldehidos aromáticos. A los compuestos (1), (2) y (3) se les evalúo su actividad antimalárica in vitro frente a las cepas FCB-2 (resistente a la cloroquina) y NF-54 de P. falciparum (sensible a la cloroquina) empleando el método radioisotópico. Se encontraron valores de IC50 entre 50,19 y 38,46 μM para la cepa FCB-2 y entre 52,49 y 33,70μM para NF-54. Las estirilquinolinas mostraron altos porcentajes de inhibición y rendimientos de reacción entre el 60 y 75%, y las estructuras de cada uno de los productos sintetizados se confirmaron mediante métodos espectroscópicos, principalmente resonancia magnética nuclear. El compuesto (3) mostró la mayor actividad antimalárica con IC50= 38,46μM para la cepa FCB-2 y 33,70μM para NF-54.

• English

  With the aim of finding novel active molecules on malaria, three styrylquinolines were synthesized: (1) 2-[(E)-2-(2-methoxyphenyl)ethenyl]quinolone, (2) 2-[(E)-2-(2-chlorophenyl)ethenyl]quinolone and (3) 2-[(E)-2-(4-isopropylphenyl)ethenyl]quinolones. For this, Perkin type condensation reactions between quinaldine and the aromatic aldehydes were done. The antimalarial activity in vitro of the compounds (1), (2) and (3) against strains FCB-2 (resistant to chloroquine) and NF-54 of P. falciparum (sensitive to chloroquine) were evaluated by radioisotopic methods. The values IC50 obtained for the strain FCB-2 were between 50.19 y 38.46μM; and between for NF-54 were from 52.49 to 33.70 μM. The styrilquinolines showed high percentages of inhibition and reaction yields between 60% and 75%, and the structures of the synthesized products were confirmed by spectral methods, mainly nuclear magnetic resonance. The compound (3) showed the highest antimalarial activity with IC50= 38.46μM for the strain FCB-2 and 33.70pM for NF-54.