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Synthesis and leishmanicidal activity of quinoline–triclosan and quinoline–eugenol hybrids

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Abstract

In this study, hybrids 7–12 and 19–24 were synthesized via Williamson reaction of O-Quinaldine alkyl bromide plus eugenol and O-triclosan alkyl bromide plus 8-hydroxyquinaldine, respectively. Structures of the products were elucidated by spectroscopic analysis. The compounds synthesized were evaluated for antileishmanial activity against L. panamensis amastigotes and cytotoxic activity against U-937 cells. The compounds 19, 20, and 21 that are 8-hydroxyquinaldine linked to triclosan by 3, 4, and 5-carbon space, respectively, were more active against axenic amastigotes (EC 50 = 23.6, 9.7, and 4.1 μg/ml, respectively). Compounds 19 and 21 were also active against intracellular amastigotes with EC 50 vales of 6.4 and 2.4 μg/ml, respectively, making these compounds promising for the development of new antileishmanial drugs.

Graphical Abstract

Quinoline–triclosan and quinoline–eugenol hybrids were obtained using Williamson etherification reactions. Leishmanicidal activity and cytotoxicity of these compounds are reported.

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Acknowledgment

The authors thank Blandine Séon-Méniel for the help during NMR measurements. This research was supported financially by the Universidad de Antioquia (Programa de Sostenibilidad).

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Authors and Affiliations

  1. Instituto de Química, Química de Plantas Colombianas, Universidad de Antioquia, A. A 1226, Medellín, Colombia

    Victor Arango, Jorge J. Domínguez, Wilson Cardona & Jairo Sáez

  2. Programa de Estudio y Control de Enfermedades Tropicales (PECET), Universidad de Antioquia, A. A 1226, Medellín, Colombia

    Sara M. Robledo & Diana L. Muñoz

  3. Laboratoire de Pharmacognosie, Associe′ au CNRS (BIOCIS), Universite′ de Paris-Sud, 92296, Chatenay-Malabry, France

    Bruno Figadere

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  1. Victor Arango
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  2. Jorge J. Domínguez
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  3. Wilson Cardona
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Correspondence to Wilson Cardona.

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Arango, V., Domínguez, J.J., Cardona, W. et al. Synthesis and leishmanicidal activity of quinoline–triclosan and quinoline–eugenol hybrids. Med Chem Res 21, 3445–3454 (2012). https://doi.org/10.1007/s00044-011-9886-8

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  • DOI: https://doi.org/10.1007/s00044-011-9886-8

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