Molecules 2012, 17(11), 12961-12973; doi:10.3390/molecules171112961
Article

4-(1H-Pyrazol-1-yl) Benzenesulfonamide Derivatives: Identifying New Active Antileishmanial Structures for Use against a Neglected Disease

Roberta K. F. Marra 1 email, Alice M. R. Bernardino 1,* email, Tathiane A. Proux 2 email, Karen S. Charret 3 email, Marie-Luce F. Lira 2 email, Helena C. Castro 2,* email, Alessandra M. T. Souza 4 email, Cesar D. Oliveira 1 email, Júlio C. Borges 1 email, Carlos R. Rodrigues 4 email, Marilene M. Canto-Cavalheiro 3 email, Leonor L. Leon 3 email and Veronica F. Amaral 2,* email
1 Programa de Pós-graduação em Química, Instituto de Química, Universidade Federal Fluminense, Outeiro de São João Baptista, Niterói, RJ, 24020-150, Brazil 2 Programa de Pós-graduação em Ciências e Biotecnologia PPBI, Instituto de Biologia, Universidade Federal Fluminense, Outeiro de São João Baptista, Niterói, RJ, 24020-150, Brazil 3 Laboratório de Bioquímica de Tripanosomatídeos, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, RJ, 21040-900, Brazil 4 Faculdade de Farmácia, ModMolQSAR, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ, 21941-590, Brazil
* Authors to whom correspondence should be addressed.
Received: 30 August 2012; in revised form: 8 October 2012 / Accepted: 12 October 2012 / Published: 1 November 2012
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Abstract: Leishmaniasis is a neglected disease responsible for about 56,000 deaths every year. Despite its importance, there are no effective, safe and proper treatments for leishmaniasis due to strain resistance and/or drug side-effects. In this work we report the synthesis, molecular modeling, cytotoxicity and the antileishmanial profile of a series of 4-(1H-pyrazol-1-yl)benzenesulfonamides. Our experimental data showed an active profile for some compounds against Leishmania infantum and Leishmania amazonensis. The profile of two compounds against L. infantum was similar to that of pentamidine, but with lower cytotoxicity. Molecular modeling evaluation indicated that changes in electronic regions, orientation as well as lipophilicity of the derivatives were areas to improve the interaction with the parasitic target. Overall the compounds represent feasible prototypes for designing new molecules against L. infantum and L. amazonensis.
Keywords: pyrazoles; benzenesulfonamide; Leishmania; cytotoxicity; in silico evaluation

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MDPI and ACS Style

Marra, R.K.F.; Bernardino, A.M.R.; Proux, T.A.; Charret, K.S.; Lira, M.-L.F.; Castro, H.C.; Souza, A.M.T.; Oliveira, C.D.; Borges, J.C.; Rodrigues, C.R.; Canto-Cavalheiro, M.M.; Leon, L.L.; Amaral, V.F. 4-(1H-Pyrazol-1-yl) Benzenesulfonamide Derivatives: Identifying New Active Antileishmanial Structures for Use against a Neglected Disease. Molecules 2012, 17, 12961-12973.

AMA Style

Marra RKF, Bernardino AMR, Proux TA, Charret KS, Lira M-LF, Castro HC, Souza AMT, Oliveira CD, Borges JC, Rodrigues CR, Canto-Cavalheiro MM, Leon LL, Amaral VF. 4-(1H-Pyrazol-1-yl) Benzenesulfonamide Derivatives: Identifying New Active Antileishmanial Structures for Use against a Neglected Disease. Molecules. 2012; 17(11):12961-12973.

Chicago/Turabian Style

Marra, Roberta K.F.; Bernardino, Alice M.R.; Proux, Tathiane A.; Charret, Karen S.; Lira, Marie-Luce F.; Castro, Helena C.; Souza, Alessandra M.T.; Oliveira, Cesar D.; Borges, Júlio C.; Rodrigues, Carlos R.; Canto-Cavalheiro, Marilene M.; Leon, Leonor L.; Amaral, Veronica F. 2012. "4-(1H-Pyrazol-1-yl) Benzenesulfonamide Derivatives: Identifying New Active Antileishmanial Structures for Use against a Neglected Disease." Molecules 17, no. 11: 12961-12973.

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