Issue 6, 2011
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MedChemComm

Sulfonyl-hydrazones of cyclic imides derivatives as potent inhibitors of the Mycobacterium tuberculosisprotein tyrosine phosphatase B (PtpB)†

Kely Navakoski de Oliveira,a   Louise Domeneghini Chiaradia,a   Priscila Graziela Alves Martins,b   Alessandra Mascarello,a   Marlon Norberto Sechini Cordeiro,a   Rafael Victorio Carvalho Guido,c   Adriano Defini Andricopulo,c   Rosendo Augusto Yunes,a   Ricardo José Nunes,a   Javier Vernalb  and  Hernán Terenzi*b  

* Corresponding authors

a Laboratório Estrutura e Atividade, Departamento de Química, LEAT-CFM-UFSC, Universidade Federal de Santa Catarina, Campus Trindade, Florianópolis, SC, Brasil

b Centro de Biologia Molecular Estrutural, Departamento de Bioquímica, CEBIME-CCB-UFSC, Universidade Federal de Santa Catarina, Campus Trindade, Florianópolis, SC, Brasil
E-mail: hterenzi@ccb.ufsc.br
Fax: +55 48 3721 6973
Tel: +55 48 3721 6426

c Laboratório de Química Medicinal e Computacional, Centro de Biotecnologia Molecular Estrutural, Instituto de Física de São Carlos, Universidade de São Paulo, Av. Trabalhador São-carlense 400, São Carlos, SP, Brazil

Abstract

Searching lead compounds for new antituberculosis drugs, the activity of synthetic sulfonamides and sulfonyl-hydrazones were assayed for their potential inhibitory activity towards a protein tyrosine phosphatase from Mycobacterium tuberculosis – PtpB. Four sulfonyl-hydrazones N-phenylmaleimide derivatives were active (compounds 14, 15, 19 and 21), and the inhibition of PtpB was found to be competitive with respect to the substrate p-nitrophenyl phosphate. Structure-based molecular docking simulations were performed and indicated that the new inhibitor candidates showed similar binding modes, filling the hydrophobic pocket of the protein by the establishment of van der Waals contacts, thereby contributing significantly to the complex stability.

Graphical abstract: Sulfonyl-hydrazones of cyclic imides derivatives as potent inhibitors of the Mycobacterium tuberculosisprotein tyrosine phosphatase B (PtpB)

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Article information

DOI
https://doi.org/10.1039/C0MD00253D
Article type
Concise Article
Submitted
08 Dec 2010
Accepted
28 Feb 2011
First published
17 Mar 2011

Med. Chem. Commun., 2011,2, 500-504

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Sulfonyl-hydrazones of cyclic imides derivatives as potent inhibitors of the Mycobacterium tuberculosisprotein tyrosine phosphatase B (PtpB)

K. Navakoski de Oliveira, L. D. Chiaradia, P. G. Alves Martins, A. Mascarello, M. N. Sechini Cordeiro, R. V. Carvalho Guido, A. D. Andricopulo, R. A. Yunes, R. J. Nunes, J. Vernal and H. Terenzi, Med. Chem. Commun., 2011, 2, 500 DOI: 10.1039/C0MD00253D

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