Síntesis y Actividad Antimalárica de Estirilquinolinas sobre Plasmodium falciparum

Santafé, Gílmar; Sánchez, Emy Luz; Torres, Omar

doi:10.4067/s0718-07642016000200012

Cited by 5 publications

(5 citation statements)

References 22 publications

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“…La asignación de las estructuras se realizó mediante el análisis de los datos espectroscópicos, apoyados en reportes similares de otros autores (Soto et al, 2011;Torres et al, 2014;Santafé et al, 2016).…”

Section: Resultados Y Discusiónunclassified

“…Sánchez et al (2014), sintetizaron y caracterizaron tres estirilquinolinas, las cuales mostraron mediante evaluación in vitro que el compuesto 2-[(E)-2-(2,3-diacetil-oxifenil)etenil] quinolina presentó una gran actividad contra Leishmania (Viannia) panamensis con un IC50 de 1.4 µg/mL e índice de selectividad (IS) de 3.9. Posteriormente mediante la aplicación del mismo método se sintetizó la estirilquinolína 2-[(E)-2-(4-isopropilfenil) etenil] quinolina que presentó gran actividad antimalárica in vitro con valores IC50 de 38.46 µg/mL frente a FCB-2 resistente a la cloroquina y 33.70 μM frente a la cepa NF-54 sensible a la cloroquina (Santafé et al, 2016). De acuerdo con lo expuesto anteriormente, es importante continuar sintetizando moléculas tipo estirilquinolinas con el fin de encontrar compuestos con mejor actividad sobre amastigotes intracelulares de L. (V) panamensis.…”

Section: Introductionunclassified

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Síntesis de estirilquinolinas con potencial Leishmanicida in vitro sobre Leishmania (Viannia) panamensis

et al. 2020

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A partir de la reacción de condensación tipo Perkin entre quinaldina y la 8-hidroxiquinaldina con aldehídos aromáticos se sintetizaron tres estirilquinolinas: (E)-2-etoxi-4-(2-(8-hidroxiquinolin-2-il)vinil)fenil acetato (1), 2-[(E)-2-(2-acetiloxi-5-nitrofenil)etenil] quinolina (2), 2-[(E)-2-(3-metoxifenil)etenil] quinolina (3). Se determinó potencial leishmanicida in vitro empleando citometría de flujo y citotoxicidad por el método MTT. Los compuestos (1) y (2) mostraron ser activos contra Leishmania (V) panamensis con valores de concentración letal 50% (CL50) de 0.2 y 2.5 µg/mL, CL50 de 2.8 y 5.9 µg/mL e índices de selectividad de 14.0 y 2.4, respectivamente, comparados con el medicamento control anfotericina B. Las estructuras de estos compuestos se confirmaron empleando técnicas espectroscópicas de análisis como IR, RMN-1 H y 13 C, COSY, HMQC, HMBC y experimentos DEPT. Se sintetizaron tres estirilquinolinas con rendimientos de 40.3%, 72.0% y 80.0% respectivamente, las estirilquinolinas (1) y (2) mostraron buen potencial leishmanicida con porcentajes de inhibición de 67.5 y 74.9 respectivamente.

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Section: Resultados Y Discusiónunclassified

Section: Introductionunclassified

Síntesis de estirilquinolinas con potencial Leishmanicida in vitro sobre Leishmania (Viannia) panamensis

et al. 2020

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“…The organic phase was dried over anhydrous sodium sulphate, ltered, and concentrated under reduced pressure. Then, the crude product was puri ed by column chromatography (CC), using petroleum benzine/ethyl acetate with an increasing polarity gradient as eluent 12,17,19 4 Hz, H 2' ), 7.28 (d, 1H, J = 9.0 Hz, Ar -H 3" ), 7.81 (dt, 1H, J = 8.3; 10.2 Hz, Ar-H 4" ), 7.34 (dt, 1H, J = 6.1; 6.8 Hz, Ar -H 5" ), 7.14 (dd, 1H, J = 7.8; 7.9 Hz, Ar -H 6" ), 13…”

Section: Methodsmentioning

confidence: 99%

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Espinosa-Saez,

Robledo,

Pineda

et al. 2023

Preprint

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In this study, six analogs of 2-arylquinoline were synthesized and evaluated for their in vitro and in vivo antiplasmodial and leishamanicidal activity. Also, hemolytic activity and drugability were tested in vitro and in silico, respectively. In relationship to leishmanicidal activity, the compounds showed half maximal effective concentration (EC50) values between 3.6µM and 19.3µM. Likewise, treatment using compounds 4a-f caused improvement in most of treated hamsters and cured some of them. Regarding antiplasmodial activity, the compounds showed moderate to high activity, did not show hemolytic activity. Furthermore, 4e and 4f compounds were not able to control P. berghei infection when administered to animal models. Molecular dynamic simulations, molecular docking and ligand binding affinity indicate good bioavailability and absorption characteristics of the studied compounds, which are expected to be active when administered orally. The compounds are absorbable at the hematoencephalic barrier but not in the gastrointestinal tract. ADMET properties suggest that these molecules may be used as a safe treatment for Leishmania.

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“…The organic phase was dried over anhydrous sodium sulphate, filtered, and concentrated under reduced pressure. Then, the crude product was purified by column chromatography (CC), using petroleum benzine/ethyl acetate with an increasing polarity gradient as eluent 12 , 17 , 19 . The chemical structures of the compounds were corroborated by NMR spectroscopic techniques: in one dimension ( 1 H, and 13 C) and two dimensions (COSY, HSQC, and HMBC), The individual data are described below:…”

Section: Methodsmentioning

confidence: 99%

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Espinosa-Saez,

Robledo,

Pineda

et al. 2023

Sci Rep

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In this study, six analogs of 2-arylquinoline were synthesized and evaluated for their in vitro and in vivo antiplasmodial and leishmanicidal activity. At a later stage, hemolytic activity and druggability were tested in vitro and in silico, respectively, observing as a result: firstly, compounds showed half-maximal effective concentration (EC50) values between 3.6 and 19.3 µM. Likewise, a treatment using the compounds 4a–f caused improvement in most of the treated hamsters and cured some of them. Regarding the antiplasmodial activity, the compounds showed moderate to high activity, although they did not show hemolytic activity. Furthermore, 4e and 4f compounds were not able to control P. berghei infection when administered to animal models. Molecular dynamic simulations, molecular docking and ligand binding affinity indicate good characteristics of the studied compounds, which are expected to be active. And lastly, the compounds are absorbable at the hematoencephalic barrier but not in the gastrointestinal tract. In summary, ADMET properties suggest that these molecules may be used as a safe treatment against Leishmania.

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Síntesis y Actividad Antimalárica de Estirilquinolinas sobre Plasmodium falciparum

Cited by 5 publications

References 22 publications

Síntesis de estirilquinolinas con potencial Leishmanicida in vitro sobre Leishmania (Viannia) panamensis

Síntesis de estirilquinolinas con potencial Leishmanicida in vitro sobre Leishmania (Viannia) panamensis

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

Screening of the antileishmanial and antiplasmodial potential of synthetic 2-arylquinoline analogs

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