Síntese de análogos de quinolina com actividade leishmanicida in vitro em Leishmania (Viannia) panamensis
Três estirilquinolinas foram sintetizadas a partir da reação de condensação do tipo Perkin entre quinaldina e 8-hidroxiquinolina com aldeídos aromáticos: (E) -2-etoxi-4-(2-(8-hidroxiquinolin-2-il) vinil) acetato de fenil (1) , 2-[(E)-2-(2-acetiloxi-5-nitrofenil) etenil] quinolina (2), 2-[(E)-2-(3-metoxifenil) etenil] quinolina (3), Leishmanicida in vitro o potencial foi determinado por citometria de fluxo e a citotoxicidade pelo método MTT. Os compostos (1) e (2) mostraram ser ativos contra Leishmania (V) panamensis com valores de EC50 de 0,2 e 2,5 µg / mL, LC50 de 2,8 e 5,9 µg / mL e índices de seletividade de 14,0 e 2,4, respectivamente, em comparação com o fármaco controle anfotericina B. As estruturas desses compostos foram confirmadas usando técnicas de análise espectroscópica, como IR, 1H e 13C NMR, COSY, HMQC, HMBC e experimentos DEPT. Três estirilquinolinas foram sintetizadas com rendimentos de 40,3%, 72,0% e 80,0% respectivamente, as estirilquinolinas (1) e (2) apresentaram bom potencial leishmanicida com percentuais de inibição de 67,5 e 74,9, respectivamente
Síntese de análogos de quinolina com actividade leishmanicida in vitro em Leishmania (Viannia) panamensis
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DOI: 10.22533/at.ed.61821061210
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Palavras-chave: Leishmania, estiril quinolinas, Reacción de tipo Perkin, Potencial leishmanicida
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Keywords: Leishmania, styrylquinolines, Perkin reaction, leishmanicidal potential
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Abstract:
Perkin type condensation reaction between quinaldine and 8-hydroxyquinaldine with aromatic aldehydes were synthesized three styrylquinolines: (E)-2-ethoxy-4-(2-(8-hydroxyquinolin-2-il)vinyl)phenyl acetate (1), 2-[(E)-2-(2-acetiloxy-5-nitrophenyl)ethenyl] quinoline (2), 2-[(E)-2-(3-methoxyiphenyl)ethenyl] quinoline (3), was determined the leishmanicidal potential in vitro applying of flow cytometry and evaluating cytotoxicity by MTT method. The compounds (1) y (2) showed to be active against Leishmania (V) panamensis with EC50 de 0.2 and 2.5 µg/mL, LC50 de 2.8 and 5.9 µg/mL and selectivity index of 14.0 and 2.4, respectively, compared to the drug control amphotericin B. The structures of these compounds were confirmed using spectroscopic techniques from analysis: IR, 1H and 13C NMR, COSY, HMQC, HMBC and DEPT experiments. Three styrylquinolines were synthesized with performence of 40.3%, 72.0% and 80.0% respectively, styrylquinolines (1) and (2) showed good leishmanicidal potential with inhibition percentages of 67.5 y 74.9 respectively.
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Número de páginas: 15
- Gilmar Gabriel Santafé Patiño
- Sara María Robledo Restrepo
- Fernis José Marin Severiche
