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Pseudo-peptides derived from isomannide: inhibitors of serine proteases

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Abstract

In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.

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Acknowledgments

This work was financially supported by CAPES, CNPq and FAPERJ. We thank to Paulo Carvalho (University of Mississippi) and Marcos Nogueira Eberlin (USP) for HRMS.

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Authors and Affiliations

  1. Faculdade de Farmácia, Universidade Federal Fluminense (UFF), Rua Mario Viana 523, Santa Rosa, Niterói, RJ, 24241000, Brazil

    Thalita G. Barros & Estela M. F. Muri

  2. Instituto de Química, Campus do Valonguinho, UFF, Niterói, RJ, Brazil

    Thalita G. Barros & Sergio Pinheiro

  3. Department of Medicinal Chemistry, School of Pharmacy, University of Mississippi, University, MS, USA

    J. S. Williamson

  4. Laboratório de Virologia Molecular, ICB, UFRJ, Rio de Janeiro, RJ, Brazil

    Amílcar Tanuri, Helena S. Pereira, R. M. Brindeiro & José B. A. Neto

  5. Instituto de Química, UFRJ, Rio de Janeiro, RJ, Brazil

    M. Gomes Jr & O. A. C. Antunes

  6. Faculdade de Odontologia de Nova Friburgo, Universidade Federal Fluminense (FOUFF), Nova Friburgo, RJ, Brazil

    Helena S. Pereira

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  1. Thalita G. Barros
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  2. Sergio Pinheiro
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  3. J. S. Williamson
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  4. Amílcar Tanuri
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  5. M. Gomes Jr
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  7. R. M. Brindeiro
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  8. José B. A. Neto
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  9. O. A. C. Antunes
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  10. Estela M. F. Muri
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Correspondence to Estela M. F. Muri.

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Barros, T.G., Pinheiro, S., Williamson, J.S. et al. Pseudo-peptides derived from isomannide: inhibitors of serine proteases. Amino Acids 38, 701–709 (2010). https://doi.org/10.1007/s00726-009-0273-4

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  • DOI: https://doi.org/10.1007/s00726-009-0273-4

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