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Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones

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Abstract

Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.

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References

  1. L.I. López, E. Leyva, R. García de la Cruz, Rev. Mex. Cienc. Farm. 42, 6 (2011)

    Google Scholar 

  2. N. El-Najjar, H. Gali-Muhtasib, R.A. Ketola, P. Vuorela, A. Urtti, H. Vuorela, Phytochem. Rev. 10, 353 (2011)

    Article  CAS  Google Scholar 

  3. S.E. Loredo-Carrillo, E. Leyva, Naftoquinonas metodologías de síntesis y propiedades fotofísicas (Verlag/Publicia, Berlin, 2015)

    Google Scholar 

  4. T. Tran, E. Saheba, A.V. Arcerio, V. Chavez, Q. Li, L.E. Martínez, T.P. Primm, Bioorg. Med. Chem. 12, 4809 (2004)

    Article  CAS  Google Scholar 

  5. G.J. Kapadia, M.A. Azuine, V. Balasubramanian, R. Sridhar, Pharmacol. Res. 43, 363 (2001)

    Article  CAS  Google Scholar 

  6. M.H. Khraiwesh, C.M. Lee, Y. Brandy, E.S. Akinboye, S. Berhe, G. Gittens, M.M. Abbas, F.R. Ampy, M. Ashraf, O. Bakare, Arch. Pharm. Res. 35, 27 (2012)

    Article  CAS  Google Scholar 

  7. C. Ibis, A. Fatih Tuyun, Z. Ozsoy-Gunes, H. Bahar, M.V. Stasevych, R. Musyanovych, O. Komarovska-Porokhnyavets, V. Novikov, Eur. J. Med. Chem. 46, 5861 (2011)

    Article  CAS  Google Scholar 

  8. R.R. Kitagawa, C. Bonacorsi, L.M. da Fonseca, W. Vilegas, M.S.G. Raddi, Rev. Bras. Farmacogn. Braz. J. Pharmacogn. 22, 53 (2012)

    Article  CAS  Google Scholar 

  9. T. Kayashima, M. Mori, H. Yoshida, Y. Mizushina, K. Matsubara, Cancer Lett. 278, 34 (2009)

    Article  CAS  Google Scholar 

  10. N. Pradidphol, N. Kongkathip, P. Sittikul, N. Boonyalai, B. Kongkathip, Eur. J. Med. Chem. 49, 253 (2012)

    Article  CAS  Google Scholar 

  11. C.-K. Ryu, J.-Y. Shim, M.-J. Chae, I.-H. Choi, J.-Y. Han, O.-J. Jung, J.-Y. Lee, S.-H. Jeong, Eur. J. Med. Chem. 40, 438 (2005)

    Article  CAS  Google Scholar 

  12. V.K. Tandon, H.K. Maurya, M.K. Verma, R. Kumar, P.K. Shukla, Eur. J. Med. Chem. 45, 2418 (2010)

    Article  CAS  Google Scholar 

  13. A.L. Lourenco, P.A. Abreu, B. Leal, E.N. da Silva Jr., A.V. Pinto, M.C.F.R. Pinto, A.M.T. Souza, J.S. Novais, M.B. Paiva, L.M. Cabral, C.R. Rodrigues, V.F. Ferreira, H.C. Castro, Curr. Microbiol. 62, 684 (2011)

    Article  CAS  Google Scholar 

  14. V.K. Tandon, H.K. Maurya, N.N. Mishra, P.K. Shukla, Bioorg. Med. Chem. Lett. 21, 6398 (2011)

    Article  CAS  Google Scholar 

  15. P. Sudbery, N. Gow, J. Berman, J. Trends Microbiol. 12, 317 (2004)

    Article  CAS  Google Scholar 

  16. A. Pugliese, D. Torre, F.M. Baccino, G. di Perri, C. Cantamessa, L. Gerbaudo, A. Saini, V. Vidotto, Cell Biochem. Funct. 18, 235 (2002)

    Article  Google Scholar 

  17. A. Mane, S. Gaikwad, S. Bembalkar, A. Risbud, J. Med. Microbiol. 61, 285 (2012)

    Article  CAS  Google Scholar 

  18. R. Faraji, M.A. Rahimi, F. Rezvanmadani, M. Hashemi, Afr. J. Microbiol. Res. 6, 2773 (2012)

    Google Scholar 

  19. M.E.L. Consolaro, T.A. Albertoni, A.E. Svidzinski, R.M. Peralta, Mycopathologia 159, 501 (2005)

    Article  CAS  Google Scholar 

  20. M.A. Pfaller, D.J. Diekema, Clin. Microbiol. Rev. 20, 133 (2007)

    Article  CAS  Google Scholar 

  21. C.A. Sable, K.M. Strohmaier, J.A. Chodakewitz, Annu. Rev. Med. 59, 361 (2008)

    Article  CAS  Google Scholar 

  22. F.C. Odds, Future Microbiol. 5, 67 (2010)

    Article  CAS  Google Scholar 

  23. A. MacCallum, Chapter 5. Candida albicans: new insights in infection, disease, and treatment, in New Insights in Medical Mycology, ed. by K. Kavanagh (Springer, Berlin, 2007)

    Google Scholar 

  24. S.K. Pitman, R.H. Drew, J.R. Perfect, Expert Opin. Emerg. Drugs 16, 559 (2011)

    Article  CAS  Google Scholar 

  25. S.P. Saville, A.L. Lazzell, C. Monteagudo, J.L. Lopez-Ribot, Eukaryot. Cell 2, 1053 (2003)

    Article  CAS  Google Scholar 

  26. M. Whiteway, U. Oberholzer, Curr. Opin. Microbiol. 7, 350 (2004)

    Article  CAS  Google Scholar 

  27. M. Whiteway, C. Bachewich, Annu. Rev. Microbiol. 61, 529 (2007)

    Article  CAS  Google Scholar 

  28. E. Manavathu, C. Duncan, Q. Porte, M. Gunasekaran, Mycopathologia 135, 79 (1996)

    Article  CAS  Google Scholar 

  29. S.K. Biswas, K. Yokoyama, K. Kamei, K. Nishimura, M. Miyaji, Med. Mycol. 39, 283 (2001)

    Article  CAS  Google Scholar 

  30. P. McGeady, D.L. Wansley, D.A. Logan, J. Nat. Prod. 65, 953 (2002)

    Article  CAS  Google Scholar 

  31. C.A. Baker, K. Desrosiers, J.W. Dolan, Antimicrob. Agents Chemother. 46, 3617 (2002)

    Article  CAS  Google Scholar 

  32. T.G. Brayman, J.W. Wilks, Antimicrob. Agents Chemother. 47, 3305 (2003)

    Article  CAS  Google Scholar 

  33. M. Matsuoka, T. Takei, T. Kitao, Chem. Lett. 8, 627 (1979)

    Article  Google Scholar 

  34. J.W. Macleod, R.H.J. Thomson, Org. Chem. 25, 36 (1960)

    Article  CAS  Google Scholar 

  35. A.A. Kutyrev, Tetrahedron 47, 8043 (1991)

    Article  CAS  Google Scholar 

  36. Y.T. Pratt, J. Org. Chem. 27, 3905 (1962)

    Article  CAS  Google Scholar 

  37. E. Leyva, L.I. López, E. Moctezuma, H. de Lasa, Top. Catal. 49, 281 (2008)

    Article  CAS  Google Scholar 

  38. E. Leyva, L.I. López, S.E. Loredo-Carrillo, M. Rodríguez-Kessler, A. Montes-Rojas, J. Fluor. Chem. 132, 94 (2011)

    Article  CAS  Google Scholar 

  39. L.I. López, J.J. Vaquera-García, A. Sáenz-Galindo, S.Y. Silva-Belmares, Lett. Org. Chem. 11, 573 (2014)

    Article  Google Scholar 

  40. E. Leyva, S.J.S. Sobeck, S.E. Loredo-Carrillo, D.A. Magaldi-Lara, J. Mol. Struct. 1068, 1 (2014)

    Article  CAS  Google Scholar 

  41. E. Leyva, K.M. Baines, C.G. Espinosa-González, D.A. Magaldi-Lara, S.E. Loredo-Carrillo, T.A. De Luna-Méndez, L.I. López, J. Fluor. Chem. 180, 152 (2015)

    Article  CAS  Google Scholar 

  42. T. Win, S. Bittner, Tetrahedron Lett. 46, 3229 (2005)

    Article  CAS  Google Scholar 

  43. L.I. López, Doctorate thesis, University of San Luis Potosí (2008)

  44. T. Win, S. Yerushalmi, S. Bittner, Synthesis 10, 1631 (2005)

    Google Scholar 

  45. E. Leyva, K.M. Baines, C.G. Espinosa-González, L.I. López, D.A. Magaldi-Lara, S. Leyva, Tetrahedron Lett. 56, 5248 (2015)

    Article  CAS  Google Scholar 

  46. H.-X. Chang, T.-C. Chou, N. Savaraj, L.F. Liu, C. Yu, C.C. Cheng, J. Med. Chem. 42, 405 (1999)

    Article  Google Scholar 

  47. M.V. Elorza, H. Rico, D. Gozalbo, R. Sentandreu, R. Antonie van Leeuwenhoek, J. Microbiol. Serol. 49, 457 (1983)

    CAS  Google Scholar 

  48. K.L. Lee, H.R. Buckley, C.C. Campbell, Sabouraudia 13, 148 (1975)

    Article  CAS  Google Scholar 

  49. M. Aguilar-Martínez, G. Cuevas, M. Jiménez-Estrada, I. González, B. Lotina-Hennsen, N.J. Macías-Ruvalcaba, J. Org. Chem. 64, 3684 (1999)

    Article  Google Scholar 

  50. S. Vega-Rodríguez, R. Jiménez-Cataño, E. Leyva, S.E. Loredo-Carrillo, J. Fluor. Chem. 145, 58 (2013)

    Article  Google Scholar 

  51. C. Frontana, I. González, J. Braz. Chem. Soc. 16, 299 (2005)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by CONACyT (Grant 155678). C.G.E.G. acknowledges financial support by CONACyT (Scholarship 219858-290917).

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Authors and Affiliations

  1. Facultad de Ciencias Químicas, Universidad Autónoma de San Luis Potosí, Av. Manuel Nava No. 6, Zona Universitaria, C.P. 78210, San Luis Potosí, S.L.P, Mexico

    Elisa Leyva, Ramón F. García de la Cruz & Claudia G. Espinosa-González

  2. Facultad de Ciencias Químicas, Universidad Autónoma de Coahuila, Blvd. V. Carranza e Ing. José Cárdenas s/n, Col República, C.P. 25250, Saltillo, Coahuila, Mexico

    Lluvia I. López

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  1. Elisa Leyva
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  2. Lluvia I. López
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  3. Ramón F. García de la Cruz
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  4. Claudia G. Espinosa-González
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Correspondence to Elisa Leyva.

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Leyva, E., López, L.I., de la Cruz, R.F.G. et al. Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones. Res Chem Intermed 43, 1813–1827 (2017). https://doi.org/10.1007/s11164-016-2732-3

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