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Insights on a new sulfonamide chalcone with potential antineoplastic application

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Abstract

Chalcones (E)-1,3-diphenyl-2-propene-1-ones, a class of biosynthetic precursor molecules of flavonoids, have a wide variety of biological applications. Besides the natural products, many synthetic derivatives and analogs became an object of continued interest in academia and industry. In this work, a synthesis and an extensive structural study were performed on a sulfonamide chalcone 1-Benzenesulfonyl-3-(4-bromobenzylidene)-2-(2-chlorophenyl)-2,3-dihydro-1H-quinolin-4-one with potential antineoplastic application. In addition, in silico experiments have shown that the sulfonamide chalcone fits well in the ligand-binding site of EGFR with seven μ-alkyl binding energy interactions on the ligand-binding site. Finally, the kinetic stability and the pharmacophoric analysis for EGFR indicated the necessary spatial characteristics for potential activity of sulfonamide chalcone as an antagonist.

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Data availability

CCDC code 2070179, available at Cambridge Crystallography Data Center.

Code availability

N/A

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Acknowledgments

This research was developed with the support of the Brazilian agencies Fundação de Amparo à Pesquisa do Estado de Goiás (FAPEG), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) and Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES). The authors thank the High Performance Computing Center of the Universidade Estadual de Goiás (UEG).

Funding

CNPq, CAPES, and FAPEG.

Author information

Authors and Affiliations

  1. Campus de Ciências Exatas e Tecnológicas, Universidade Estadual de Goiás, Anápolis, GO, Brazil

    Patricia R. S. Wenceslau, Renata L. G. de Paula, Vitor S. Duarte, Laura M. M. Guimarães, Leonardo L. Borges & Hamilton B. Napolitano

  2. Instituto de Química, Universidade Federal de Goiás, Goiânia, GO, Brazil

    Giulio D. C. D’Oliveira & Caridad N. Pérez

  3. Escola de Ciências Médicas, Farmacêuticas e Biomédicas, Pontifícia Universidade Católica de Goiás, Goiânia, GO, Brazil

    Leonardo L. Borges

  4. Universidade Evangélica de Goiás, UniEvangélica, Anápolis, GO, Brazil

    José L. R. Martins, James O. Fajemiroye, Pal Perjesi & Hamilton B. Napolitano

  5. Instituto de Ciências Biológicas, Universidade Federal de Goiás, Goiânia, GO, Brazil

    James O. Fajemiroye

  6. Departamento de Química, Universidade Federal de Juiz de Fora, Juiz de Fora, MG, Brazil

    Chris H. J. Franco

  7. Institute of Pharmaceutical Chemistry, University of Pécs, Pécs, Hungary

    Pal Perjesi

Authors
  1. Patricia R. S. Wenceslau
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  2. Renata L. G. de Paula
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  3. Vitor S. Duarte
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  4. Giulio D. C. D’Oliveira
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  5. Laura M. M. Guimarães
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  6. Caridad N. Pérez
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  7. Leonardo L. Borges
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  8. José L. R. Martins
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  9. James O. Fajemiroye
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  10. Chris H. J. Franco
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  11. Pal Perjesi
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  12. Hamilton B. Napolitano
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Contributions

Introduction: P.R.S. Wenceslau, R.L.G. Paula, V.S. Duarte, G.D.C. D’Oliveira, L.M.M. Guimarães, C.N. Pérez, L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco, P.Perjesi and H.B. Napolitano;

Crystallographic analysis: P.R.S. Wenceslau, R.L.G. Paula, V.S. Duarte, D’Oliveira, C.N. Pérez and H.B. Napolitano;

Theoretical Analysis: V.S. Duarte, C.N. Pérez, and H.B. Napolitano;

In silico bioactivity screening: L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco, P.Perjesi and H.B. Napolitano;

Pharmacophore analysis: C.N. Pérez, L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco and P.Perjesi;

Molecular docking: P.R.S. Wenceslau, R.L.G. Paula, V.S. Duarte, G.D.C. D’Oliveira, L.M.M. Guimarães, C.N. Pérez, L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco, P.Perjesi and H.B. Napolitano.

Results and discussion: P.R.S. Wenceslau, R.L.G. Paula, V.S. Duarte, G.D.C. D’Oliveira, L.M.M. Guimarães, C.N. Pérez, L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco, P.Perjesi and H.B. Napolitano.

Conclusions: P.R.S. Wenceslau, R.L.G. Paula, V.S. Duarte, G.D.C. D’Oliveira, L.M.M. Guimarães, C.N. Pérez, L.L. Borges, J.L.R. Martins, J.O. Fajemiroye, C.H.J. Franco, P.Perjesi and H.B. Napolitano.

Corresponding author

Correspondence to Hamilton B. Napolitano.

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Wenceslau, P.R.S., de Paula, R.L.G., Duarte, V.S. et al. Insights on a new sulfonamide chalcone with potential antineoplastic application. J Mol Model 27, 211 (2021). https://doi.org/10.1007/s00894-021-04818-w

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