Sulfonamide-1,2,4-thiadiazole Derivatives as Antifungal and Antibacterial Agents: Synthesis, Biological Evaluation, Lipophilicity, and Conformational Studies

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  • Camoutsis Charalabos
    School of Health Sciences, Department of Pharmacy, Laboratory of Pharmaceutical Chemistry, University of Patras
  • Geronikaki Athina
    School of Pharmacy, Department of Pharmaceutical Chemistry of Aristotelian, University of Thessaloniki
  • Ciric Ana
    Department of Plant Physiology, Mycological Laboratory, Institute of Biological Research
  • Soković Marina
    Department of Plant Physiology, Mycological Laboratory, Institute of Biological Research
  • Zoumpoulakis Panagiotis
    Laboratory of Molecular Analysis, Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation
  • Zervou Maria
    Laboratory of Molecular Analysis, Institute of Organic and Pharmaceutical Chemistry, National Hellenic Research Foundation

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A series of thirteen new thiadiazole compounds were synthesized and evaluated for in vitro antifungal and antibacterial activity. All compound tested showed significant antifungal activity against all the micromycetes, compared to the commercial fungicide bifonazole. Differences in their activity depend on the substitution of different reactive groups. More specifically, best antifungal activity was shown for the synthetic analogue with methylpiperazine reactive group. Furthermore, it is apparent that different compounds reacted on different ways against bacteria. An effort was made to correlate the above mentioned differences in activity with lipophilicity studies. Furthermore, NMR and molecular modelling were used to obtain the main conformational features of a potent analogue, for future in silico studies.

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