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2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole analogues: Antifungal activity in vitro against Candida species

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Abstract

The antifungal activity in vitro of the newly synthesized and previously reported compounds of 5-substituted 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole series was evaluated. Their structures were confirmed by elemental analyses and IR, 1H and 13C NMR and mass spectra. The azole-resistant clinical isolates of Candida albicans and no-albicans Candida spp. were used in the antifungal tests. Some compounds exhibit higher activities than the comparatively studied antifungal drugs. Amino-1,3,4-thiadiazole derivatives exhibited higher (than other analogues) antifungal effects against Candida no-albicans spp. than against C. albicans. Derivatives with strong antifungal activity have a narrow range of lipophilicity values determined by the Villar approach.

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References

  1. Collin, B., Clancy, C.J., and Hong Nguyen, M., Drug Resist. Update, 1999, vol. 2, pp. 9–14.

    Article  Google Scholar 

  2. Sanglard, D. and Odds, F.C., Lancet Infect. Dis., 2002, vol. 2, pp. 73–85.

    Article  PubMed  CAS  Google Scholar 

  3. Matysiak, J., Karczewski, J., Niewiadomy, A., and Krajewska-Kułak, E., J. Agric. Food Chem., 2001, vol. 49, pp. 5251–5257.

    Article  PubMed  CAS  Google Scholar 

  4. Matysiak, J., Niewiadomy A., Macik-Niewiadomyl G., Korniłłowiczl T., Eur. J. Med. Chem., 2000, vol. 35, pp. 393–404.

    Article  PubMed  CAS  Google Scholar 

  5. Matysiak, J. and Niewiadomy, A., Bioorg. Med. Chem., 2003, vol. 11, pp. 2285–2291.

    Article  PubMed  CAS  Google Scholar 

  6. Modzelewska-Banachiewicz, B., Matysiak, J., and Niewiadomy, A., Eur. J. Med. Chem., 2001, vol. 36, pp. 75–80.

    Article  PubMed  CAS  Google Scholar 

  7. Matysiak, J., Niewiadomy, A., Senczyna, B., Żabińska, A., and Różyło, J.K., J. AOAC Int., 2004, vol. 87, pp. 579–586.

    PubMed  CAS  Google Scholar 

  8. Matysiak, J., Bioorg. Med. Chem., 2006, vol. 14, pp. 2613–2619.

    Article  PubMed  CAS  Google Scholar 

  9. Matysiak, J., J. Heterocyclic Chem., 2006, vol. 43, pp. 55–58.

    Article  CAS  Google Scholar 

  10. Ghannoum, M.A., Abu-Elteen, K.H., Motawy, M.S., Abu-Hatab, A.S., Ibrahim, A.S., and Criddle, R.S., Chemotherapy, 1990, vol. 36, pp. 308–320.

    Article  PubMed  CAS  Google Scholar 

  11. Kasukabe, T., Okabe-Kado, J., Kato, N., Sassa, T., and Honma, Y., Breast Cancer Res., 2005, vol. 7, pp. R1097–R1110.

    Article  PubMed  CAS  Google Scholar 

  12. Cardenas, M.E., Cruz, M.C., del Poeta, M., Chung, N., Perfect, J.R., and Heitman, J., Clin. Microbiol. Rev., 1999, vol. 12, pp. 583–611.

    PubMed  CAS  Google Scholar 

  13. Holla, S.B., Rao, S.B., Gonsalves, R., Sarojini, B.K., and Shridhara, K., Farmaco, 2002, vol. 57, pp. 693–696.

    Article  PubMed  Google Scholar 

  14. Gürsoy, A., Demirayak, S., Cesur, Z., Reisch, J., and Otuk, G., Pharmazie, 1990, vol. 45, pp. 246–250.

    PubMed  Google Scholar 

  15. Mamolo, M.G., Vio, L., and Banfi, E., Farmaco, 1996, vol. 51, pp. 71–74.

    PubMed  CAS  Google Scholar 

  16. Mastrolorenzo, A., Scozzafava, A., and Supuran, C.T., J. Enzyme Inhib., 2000, vol. 15, pp. 517–531.

    Article  PubMed  CAS  Google Scholar 

  17. Rollas, S., Karakuş, S., Durgun, B.B., Kiraz, M., and Erdeniz, H., IL Farmaco, 1996, vol. 51, pp. 811–814.

    PubMed  CAS  Google Scholar 

  18. Dogan, H.N., Rollas, S., and Erdeniz, H., Farmaco, 1998, vol. 53, pp. 462–467.

    Article  PubMed  CAS  Google Scholar 

  19. Dogan, H.N., Duran, A., Rollas, S., Sener, G., Uysal, M.K., and Gulen, D., Bioorg. Med. Chem., 2002, vol. 10, pp. 2893–2898.

    Article  PubMed  CAS  Google Scholar 

  20. Foroumadi, A., Daneshtalab, M., and Shafiee, A., Arzneim.-Forsch./Drug Res., 1999, vol. 49, pp. 1035–1038.

    CAS  Google Scholar 

  21. Demirbas, N., Karaoglu, S.A., Demirbas, A., and Sancak, K., Eur. J. Med. Chem., 2004, vol. 39, pp. 793–804.

    Article  PubMed  CAS  Google Scholar 

  22. Mamolo, M.G., Falagiani, V., Zampieri, D., Vio, L., and Banfi, E., Farmaco, 2001, vol. 56, pp. 587–592.

    Article  PubMed  CAS  Google Scholar 

  23. Ayhan, Kilcigil G., Kus, C., Altanlar, N.C., and Özbey S., Turk. J. Chem., 2005, vol. 29, pp. 153–162.

    Google Scholar 

  24. Varvaresou, A., Siatra-Papastaikoudi, T., Dalla Tsotinis A., Tsantili-Kakoulidou, A., and Vamvakides, A., Farmaco, 1998, vol. 53, pp. 320–326.

    Article  PubMed  CAS  Google Scholar 

  25. Varvaresou, A., Tsantili-Kakoulidou, A., Siatra-Papastaikoudi, T., and Tiligada, E., Arzneim.-Forsch./Drug Res., 2000, vol. 50, pp. 48–54.

    CAS  Google Scholar 

  26. Servi, S., Genc, M., Gur, S., and Koca, M., Eur. J. Med. Chem., 2005, vol. 40, pp. 687–693.

    Article  PubMed  CAS  Google Scholar 

  27. Chen, H., Li, Z., and Han, Y., J. Agric. Food Chem., 2000, vol. 48, pp. 5312–5315.

    Article  PubMed  CAS  Google Scholar 

  28. Zou, X.-J., Lai, L.-H., Jin, G.-Y., and Zhang, Z.-X., J. Agric. Food Chem., 2000, vol. 50, pp. 3757–3760.

    Article  CAS  Google Scholar 

  29. Holla, S.B., Gonsalves, R., Rao, S.B., Shenoy, S., and Gopalakrishna, H.N., Farmaco, 2001, vol. 56, pp. 899–903.

    Article  PubMed  CAS  Google Scholar 

  30. Russo, F., Santagati, M., Santagati, A., and Blandino, G., Farmaco, 1981, vol. 36, pp. 983–993.

    CAS  Google Scholar 

  31. Matysiak, J. and Niewiadomy, A., Synthethic Commun., 2006, vol. 36, pp. 1621–1630.

    Article  CAS  Google Scholar 

  32. Matysiak, J., Nasulewicz, A., Pełczyńska M., Switalska, M., and Opolski, A., Eur. J. Med. Chem., 2006, vol. 41, pp. 475–482.

    Article  PubMed  CAS  Google Scholar 

  33. Kantola, A., Villar, H.O., and Loew, G.H., J. Comput. Chem., 1991, vol. 12, pp. 681–689.

    Article  CAS  Google Scholar 

  34. National Committee for Clinical Laboratory Standards, Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, Approved Standard. Document M27-A, National Committee for Clinical Laboratory Standards, Villanova, Pa, 1997.

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Correspondence to J. Matysiak.

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Original Russian Text © J. Matysiak, Z. Malinski, 2007, published in Bioorganicheskaya Khimiya, 2007, Vol. 33, No. 6, pp. 640–647.

The text was submitted by the authors in English.

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Matysiak, J., Malinski, Z. 2-(2,4-dihydroxyphenyl)-1,3,4-thiadiazole analogues: Antifungal activity in vitro against Candida species. Russ J Bioorg Chem 33, 594–601 (2007). https://doi.org/10.1134/S1068162007060106

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  • DOI: https://doi.org/10.1134/S1068162007060106

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