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Molecules 2017, 22(12), 2041; doi:10.3390/molecules22122041

Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents

1
Química Orgánica de Productos Naturales, Instituto de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Antioquia, calle 70 No. 52-21, Medellin A.A 1226, Colombia
2
PECET-Facultad de Medicina, Universidad de Antioquia, calle 70 No. 52-21, Medellin A.A 1226, Colombia
*
Authors to whom correspondence should be addressed.
Received: 24 October 2017 / Revised: 20 November 2017 / Accepted: 20 November 2017 / Published: 29 November 2017
(This article belongs to the Special Issue Focusing on Sulfur in Medicinal Chemistry)
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Abstract

The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity. View Full-Text
Keywords: Leishmania; thiochroman-4-ones; thiochromones; thioflavones; vinyl sulfone Leishmania; thiochroman-4-ones; thiochromones; thioflavones; vinyl sulfone
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Vargas, E.; Echeverri, F.; Vélez, I.D.; Robledo, S.M.; Quiñones, W. Synthesis and Evaluation of Thiochroman-4-One Derivatives as Potential Leishmanicidal Agents. Molecules 2017, 22, 2041.

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