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Open AccessArticle

Synthesis and Evaluation of Antileishmanial and Cytotoxic Activity of Benzothiopyrane Derivatives

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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, Colombia
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PECET-Facultad de Medicina, Universidad de Antioquia, calle 70 No. 52–21, Medellín A. A 1226, Colombia
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Dipartimento di Scienze Farmaceutiche, Università di Perugia, Via del Liceo, 1, 06123 Perugia, Italy
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Authors to whom correspondence should be addressed.
Academic Editors: Andrew Tsotinis and Ioannis Papanastasiou
Molecules 2020, 25(4), 800; https://doi.org/10.3390/molecules25040800 (registering DOI)
Received: 7 December 2019 / Revised: 21 January 2020 / Accepted: 30 January 2020 / Published: 12 February 2020
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.
Keywords: Leishmania; thiochromenes; benzothiopyrans; thiochroman-4-ones; synthesis; leishmaniasis; cytotoxicity Leishmania; thiochromenes; benzothiopyrans; thiochroman-4-ones; synthesis; leishmaniasis; cytotoxicity
MDPI and ACS Style

Ortiz, C.; Echeverri, F.; Robledo, S.; Lanari, D.; Curini, M.; Quiñones, W.; Vargas, E. Synthesis and Evaluation of Antileishmanial and Cytotoxic Activity of Benzothiopyrane Derivatives. Molecules 2020, 25, 800.

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