Synthesis and Evaluation of Antileishmanial and Cytotoxic Activity of Benzothiopyrane Derivatives
Cristian Ortiz,
Fernando Echeverri,
Sara Robledo,
Daniela Lanari,
Massimo Curini,
Wiston Quiñones,
Esteban Vargas
Affiliations
Cristian Ortiz
Química Orgánica de Productos Naturales, Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia, calle 70, No. 52–21, Medellín A. A 1226, Columbia
Fernando Echeverri
Química Orgánica de Productos Naturales, Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia, calle 70, No. 52–21, Medellín A. A 1226, Columbia
Sara Robledo
PECET-Facultad de Medicina, Universidad de Antioquia, calle 70 No. 52–21, Medellín A. A 1226, Columbia
Daniela Lanari
Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo, 1, 06123 Perugia, Italy
Massimo Curini
Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo, 1, 06123 Perugia, Italy
Wiston Quiñones
Química Orgánica de Productos Naturales, Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia, calle 70, No. 52–21, Medellín A. A 1226, Columbia
Esteban Vargas
Química Orgánica de Productos Naturales, Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia, calle 70, No. 52–21, Medellín A. A 1226, Columbia
In continuation of our efforts to identify promising antileishmanial agents based on the chroman scaffold, we synthesized several substituted 2H-thiochroman derivatives, including thiochromenes, thichromanones and hydrazones substituted in C-2 or C-3 with carbonyl or carboxyl groups. Thirty-two compounds were thus obtained, characterized, and evaluated against intracellular amastigotes of Leishmania (V) panamensis. Twelve compounds were active, with EC50 values lower than 40 µM, but only four compounds displayed the highest antileishmanial activity, with EC50 values below 10 µM; these all compounds possess a good Selectivity Index > 2.6. Although two active compounds were thiochromenes, a clear structure-activity relationship was not detected since each active compound has a different substitution pattern.
