Skip to main content
SpringerLink
Log in

Synthesis and First-Time Assessment of o-Eugenol Derivatives against Mycobacterium tuberculosis

  • Published:
Chemistry of Natural Compounds Aims and scope

In this work, we report the first-time assessment of o-eugenol, 6-allyl-2-methoxyphenol, and their selected derivatives, against Mycobacterium tuberculosis H37RV, using the MABA susceptibility test. The bromo, nitro, O-alkylated, and reduced derivatives were obtained by standard methods and were characterized by spectroscopic and mass spectral data. Structure–activity relationships were investigated, with the most active derivatives being 4,5-dibromo-2-methoxy-6-propylphenol (139 μM) and 2-methoxy-3-nitro-6-propylphenol (237 μM). This study provides important information on the rational design of new lead anti-TB drugs based on o-eugenol derivatives.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 3.

Similar content being viewed by others

References

  1. P. Manitto, D. Monti, and P. Gramatica, J. Chem. Soc., Perkin Trans. 1, 1, 727 (1974).

    Google Scholar 

  2. T. S. Kaufman, J. Braz. Chem. Soc., 26 (6), 1055 (2015).

    CAS  Google Scholar 

  3. C. E. Greenhalf, D. J. Nowakowski, N. Yates, I. Shield, and A. V. Bridgwater, Biomass Bioenergy, 56, 247 (2013).

    Article  CAS  Google Scholar 

  4. G. T. McQuate, Y. S. Keum, C. D. Sylva, Q. X. Li, and E. B. Jang, J. Econ. Entomol., 97 (3), 862 (2004).

    Article  CAS  Google Scholar 

  5. Y. -S. Keum, G. T. McQuate, and Q. X. Li, Biochem. Syst. Ecol., 35 (4), 188 (2007).

    Article  CAS  Google Scholar 

  6. H. Cao, L. Zuguang, and C. Xiaozhen, Chin. J. Chem., 29 (10), 2187 (2011).

    Article  CAS  Google Scholar 

  7. D.V. Fonseca, P. R. R. Salgado, H. C. A. Neto, A. M. F. O. Golzio, M. R. D. C. Filho, C. G. F. Melo, F. C. Leite, M. R. Piuvezam, L. C. M. Pordeus, J. M. B. Filho, and R. N. Almeida, Int. Immunopharmacol., 38, 402 (2016).

    Article  CAS  Google Scholar 

  8. Global Tuberculosis Report 2017, Switzerland: World Health Organization (WHO), 2017. ISBN: 978-92-4-156551-6.

  9. C. Lienhardt, M. Raviglione, M. Spigelamn, R. Hafner, E. Jaramillo, M. Hoelscher, A. Zumla, and J. Gheuens, J. Infect. Dis., 205, S241 (2012).

    Article  Google Scholar 

  10. C. F. H. Allen and J. W. Gates, Org. Synth., 25, 49 (1945).

    Article  CAS  Google Scholar 

  11. S. G. Franzblau, R. S. Witzig, J. C. McLaughlin, P. Torres, G. Madico, A. Hernandez, M. T. Degnan, M. B. Cook, V. K. Quenzer, R. M. Ferguson, and R. H. Gilman, J. Clin. Microbiol., 36 (2), 362 (1998).

    Article  CAS  Google Scholar 

  12. P. Strazzolini, A. G. Giumanini, A. Runcio, and M. Scuccato, J. Org. Chem., 63 (4), 952 (1998).

    Article  CAS  Google Scholar 

  13. C. Wermuth, D. Aldous, P. Raboisson, and D. Rognan, The Practice of Medicinal Chemistry, Academic Press, Amsterdam, 2015, 902 pp.

    Google Scholar 

  14. Y.-L. Lin, J.-Y. Chengy, and Y.-H. Chu, Tetrahedron, 63, 10949 (2007).

    Article  CAS  Google Scholar 

  15. J. D. Vanitha and C. N. Paramasivan, Mycobacteriology, 49 (3), 179 (2004).

    CAS  Google Scholar 

  16. R. S. Reis, I. Neves, S. L. S. Lourenco, L. S. Fonseca, and M. C. S. Lourenco, J. Clin. Microbiol., 42 (5), 2247 (2004).

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENT

The authors A. M. Moraes and M. V. N. de Souza are thankful to CNPq for financial support.

Author information

Authors and Affiliations

  1. Universidade Federal do Rio de Janeiro, Instituto de Quimica, Departamento de Quimica Organica, 68563, Zip Code, Rio de Janeiro, 21945-970, Brazil

    Adriana Marques Moraes

  2. Fiocruz–Fundacao Oswaldo Cruz, Instituto de Tecnologia em Farmacos – Farmanguinhos, Sizenando Nabuco 100, Manguinhos, Rio de Janeiro, 21041-250, Brazil

    Adriana Marques Moraes, Emerson Teixeira da Silva & Marcus V. N. de Souza

  3. Department of Chemistry, University of Aberdeen, Aberdeen, AB2 3UE, Scotland, UK

    James L. Wardell

Authors
  1. Adriana Marques Moraes
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Emerson Teixeira da Silva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. James L. Wardell
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Marcus V. N. de Souza
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Adriana Marques Moraes, Emerson Teixeira da Silva, James L. Wardell or Marcus V. N. de Souza.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2020, pp. 549–554.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Moraes, A.M., da Silva, E.T., Wardell, J.L. et al. Synthesis and First-Time Assessment of o-Eugenol Derivatives against Mycobacterium tuberculosis. Chem Nat Compd 56, 633–638 (2020). https://doi.org/10.1007/s10600-020-03110-2

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-020-03110-2

Keywords

Search

Navigation