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.
Similar content being viewed by others
References
Collin, B., Clancy, C.J., and Hong Nguyen, M., Drug Resist. Update, 1999, vol. 2, pp. 9–14.
Sanglard, D. and Odds, F.C., Lancet Infect. Dis., 2002, vol. 2, pp. 73–85.
Matysiak, J., Karczewski, J., Niewiadomy, A., and Krajewska-Kułak, E., J. Agric. Food Chem., 2001, vol. 49, pp. 5251–5257.
Matysiak, J., Niewiadomy A., Macik-Niewiadomyl G., Korniłłowiczl T., Eur. J. Med. Chem., 2000, vol. 35, pp. 393–404.
Matysiak, J. and Niewiadomy, A., Bioorg. Med. Chem., 2003, vol. 11, pp. 2285–2291.
Modzelewska-Banachiewicz, B., Matysiak, J., and Niewiadomy, A., Eur. J. Med. Chem., 2001, vol. 36, pp. 75–80.
Matysiak, J., Niewiadomy, A., Senczyna, B., Żabińska, A., and Różyło, J.K., J. AOAC Int., 2004, vol. 87, pp. 579–586.
Matysiak, J., Bioorg. Med. Chem., 2006, vol. 14, pp. 2613–2619.
Matysiak, J., J. Heterocyclic Chem., 2006, vol. 43, pp. 55–58.
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.
Kasukabe, T., Okabe-Kado, J., Kato, N., Sassa, T., and Honma, Y., Breast Cancer Res., 2005, vol. 7, pp. R1097–R1110.
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.
Holla, S.B., Rao, S.B., Gonsalves, R., Sarojini, B.K., and Shridhara, K., Farmaco, 2002, vol. 57, pp. 693–696.
Gürsoy, A., Demirayak, S., Cesur, Z., Reisch, J., and Otuk, G., Pharmazie, 1990, vol. 45, pp. 246–250.
Mamolo, M.G., Vio, L., and Banfi, E., Farmaco, 1996, vol. 51, pp. 71–74.
Mastrolorenzo, A., Scozzafava, A., and Supuran, C.T., J. Enzyme Inhib., 2000, vol. 15, pp. 517–531.
Rollas, S., Karakuş, S., Durgun, B.B., Kiraz, M., and Erdeniz, H., IL Farmaco, 1996, vol. 51, pp. 811–814.
Dogan, H.N., Rollas, S., and Erdeniz, H., Farmaco, 1998, vol. 53, pp. 462–467.
Dogan, H.N., Duran, A., Rollas, S., Sener, G., Uysal, M.K., and Gulen, D., Bioorg. Med. Chem., 2002, vol. 10, pp. 2893–2898.
Foroumadi, A., Daneshtalab, M., and Shafiee, A., Arzneim.-Forsch./Drug Res., 1999, vol. 49, pp. 1035–1038.
Demirbas, N., Karaoglu, S.A., Demirbas, A., and Sancak, K., Eur. J. Med. Chem., 2004, vol. 39, pp. 793–804.
Mamolo, M.G., Falagiani, V., Zampieri, D., Vio, L., and Banfi, E., Farmaco, 2001, vol. 56, pp. 587–592.
Ayhan, Kilcigil G., Kus, C., Altanlar, N.C., and Özbey S., Turk. J. Chem., 2005, vol. 29, pp. 153–162.
Varvaresou, A., Siatra-Papastaikoudi, T., Dalla Tsotinis A., Tsantili-Kakoulidou, A., and Vamvakides, A., Farmaco, 1998, vol. 53, pp. 320–326.
Varvaresou, A., Tsantili-Kakoulidou, A., Siatra-Papastaikoudi, T., and Tiligada, E., Arzneim.-Forsch./Drug Res., 2000, vol. 50, pp. 48–54.
Servi, S., Genc, M., Gur, S., and Koca, M., Eur. J. Med. Chem., 2005, vol. 40, pp. 687–693.
Chen, H., Li, Z., and Han, Y., J. Agric. Food Chem., 2000, vol. 48, pp. 5312–5315.
Zou, X.-J., Lai, L.-H., Jin, G.-Y., and Zhang, Z.-X., J. Agric. Food Chem., 2000, vol. 50, pp. 3757–3760.
Holla, S.B., Gonsalves, R., Rao, S.B., Shenoy, S., and Gopalakrishna, H.N., Farmaco, 2001, vol. 56, pp. 899–903.
Russo, F., Santagati, M., Santagati, A., and Blandino, G., Farmaco, 1981, vol. 36, pp. 983–993.
Matysiak, J. and Niewiadomy, A., Synthethic Commun., 2006, vol. 36, pp. 1621–1630.
Matysiak, J., Nasulewicz, A., Pełczyńska M., Switalska, M., and Opolski, A., Eur. J. Med. Chem., 2006, vol. 41, pp. 475–482.
Kantola, A., Villar, H.O., and Loew, G.H., J. Comput. Chem., 1991, vol. 12, pp. 681–689.
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.
Author information
Authors and Affiliations
Corresponding author
Additional information
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.
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1134/S1068162007060106