Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Gabriela Alves de Souza
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Paulo Pitasse-Santos
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Douglas Chaves de Alcântara Pinto
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Debora Decote-Ricardo
Departamento de Microbiologia e Imunologia Veterinária, Instituto de Veterinária, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Marco Edilson Freire de Lima
Departamento de Química Orgânica, Instituto de Química, Universidade Federal Rural do Rio de Janeiro, Seropédica 23890-000, Brazil
Nitroimidazoles are pharmacophoric groups responsible for important antiparasitic activity against several infectious diseases. 2-Nitroimidazoles are found in some antiparasitic drugs and are one of the main moieties responsible for the biological activities exhibited. As an example, we can mention the drug benznidazole, the only drug available in Brazil for the treatment of Chagas disease. This work describes an efficient methodology for the synthesis of 2-nitro-1-vinyl-1H-imidazole through a simple and direct approach, as well as its full characterization and biological assessment. The antiparasitic evaluation of 2-nitro-1-vinyl-1H-imidazole against Trypanosoma cruzi (Tulahuen C2C4-LacZ strain) showed IC50 = 4.8 μM on amastigotes and low cytotoxicity against LLC-MK2 cells (IC50 > 500 μM), validating 2-nitro-1-vinyl-1H-imidazole as a biologically active structural subunit for anti-T. cruzi activity. The results presented herein demonstrate that 2-nitro-1-vinyl-1H-imidazole can be easily obtained, possessing great potential for use in the design of new antichagasic drugs through a molecular hybridization strategy using known coupling reactions.
