Molecules 2018, 23(1), 177; https://doi.org/10.3390/molecules23010177
Tetrasubstituted Imidazolium Salts as Potent Antiparasitic Agents against African and American Trypanosomiases
Ouldouz Ghashghaei 1
, Nicola Kielland 1, Marc Revés 1, Martin C. Taylor 2, John M. Kelly 2, Ornella Di Pietro 3, Diego Muñoz-Torrero 3, Belén Pérez 4 and Rodolfo Lavilla 1,*
, Nicola Kielland 1, Marc Revés 1, Martin C. Taylor 2, John M. Kelly 2, Ornella Di Pietro 3, Diego Muñoz-Torrero 3, Belén Pérez 4 and Rodolfo Lavilla 1,*
1
Laboratory of Organic Chemistry, Faculty of Pharmacy and Food Sciences, University of Barcelona, Barcelona Science Park, Baldiri Reixac 10-12, 08028 Barcelona, Spain
2
Department of Pathogen Molecular Biology, London School of Hygiene and Tropical Medicine, London WC1E 7HT, UK
3
Laboratory of Pharmaceutical Chemistry (CSIC Associated Unit), Faculty of Pharmacy and Food Sciences, and Institute of Biomedicine (IBUB), University of Barcelona, 08028 Barcelona, Spain
4
Department of Pharmacology, Therapeutics and Toxicology, Institute of Neurosciences, Autonomous University of Barcelona, 08193 Bellaterra, Barcelona, Spain
*
Author to whom correspondence should be addressed.
Received: 29 November 2017 / Revised: 10 January 2018 / Accepted: 13 January 2018 / Published: 16 January 2018
(This article belongs to the Special Issue Multicomponent Reaction-Based Synthesis of Bioactive Molecules)
Abstract
Imidazolium salts are privileged compounds in organic chemistry, and have valuable biological properties. Recent studies show that symmetric imidazolium salts with bulky moieties can display antiparasitic activity against T. cruzi. After developing a facile methodology for the synthesis of tetrasubstituted imidazolium salts from propargylamines and isocyanides, we screened a small library of these adducts against the causative agents of African and American trypanosomiases. These compounds display nanomolar activity against T. brucei and low (or sub) micromolar activity against T. cruzi, with excellent selectivity indexes and favorable molecular properties, thereby emerging as promising hits for the treatment of Chagas disease and sleeping sickness. View Full-TextKeywords:
imidazolium salts; isocyanides; antiparasitic agents; Trypanosoma brucei; Trypanosoma cruzi
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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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Ghashghaei, O.; Kielland, N.; Revés, M.; Taylor, M.C.; Kelly, J.M.; Di Pietro, O.; Muñoz-Torrero, D.; Pérez, B.; Lavilla, R. Tetrasubstituted Imidazolium Salts as Potent Antiparasitic Agents against African and American Trypanosomiases. Molecules 2018, 23, 177.
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