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Medicinal Chemistry Research

, Volume 27, Issue 2, pp 497–511 | Cite as

Synthesis and antiprotozoal activity of furanchalcone–quinoline, furanchalcone–chromone and furanchalcone–imidazole hybrids

  • Elisa García
  • Juan C. Coa
  • Elver Otero
  • Miguel Carda
  • Iván D. Vélez
  • Sara M. Robledo
  • Wilson I. Cardona
Original Research

Abstract

We report herein the synthesis and biological activities (cytotoxicity, leishmanicidal, and trypanocidal) of several furanchalcone–quinoline, furanchalcone–chromone, and furanchalcone–imidazole hybrids. The synthesized compounds were evaluated against amastigotes forms of L. (V) panamensis, which is the most prevalent Leishmania species in Colombia and against Trypanosoma cruzi, which is the major pathogenic species to humans. Cytotoxicity was evaluated against human U-937 macrophages. Compounds (6e, 8a8f, 11b, and 11c) were active against both L. (V) panamensis and T. cruzi being 8e and 8f the most active compounds with an EC50 of 0.78 and 2.16 µM against L. (V) panamensis, respectively, and 0.66 and 0.72 µM against T. cruzi, respectively. Seven hybrid compounds showed better activity than meglumine antimoniate and the anti-trypanosomal activity of nine compounds were higher than benznidazole. Although these compounds showed toxicity for mammalian U-937 cells, they still have the potential to be considered as candidates for antileishmanial or trypanocydal drug development. There is not a clear relationship between the antiprotozoal activity and the length of the alkyl linker. However, we obtained higher bioactivity when the alkyl linker has nine and twelve carbon atoms. Furanchalcone-imidazole hybrids were the most active of all compounds, showing that the imidazole salt moiety is important for their biological actions.

Keywords

Leishmaniasis Chagas disease Antiprotozoal activity Furanchalcone Hybrids Quinoline 

Notes

Acknowledgements

The authors thank Universidad de Antioquia (grant CODI 6203 and CIDEPRO) for financial support.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no competing interests.

Supplementary material

44_2017_2076_MOESM1_ESM.doc (2.4 mb)
Supporting Information

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Copyright information

© Springer Science+Business Media, LLC 2017

Authors and Affiliations

  • Elisa García
    • 1
  • Juan C. Coa
    • 1
  • Elver Otero
    • 1
  • Miguel Carda
    • 2
  • Iván D. Vélez
    • 3
  • Sara M. Robledo
    • 3
  • Wilson I. Cardona
    • 1
  1. 1.Chemistry of Colombian Plants, Institute of Chemistry, School of Exact and Natural SciencesUniversity of Antioquia-UdeAMedellínColombia
  2. 2.Department of Inorganic and Organic ChemistryJaume I UniversityCastellónSpain
  3. 3.PECET-Medical Research Institute, School of MedicineUniversity of Antioquia-UdeAMedellínColombia

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