Síntese e avaliação da atividade antifúngica de isatina-aril-tiossemicarbazonas

Abstract

Hybrid compounds such as isatin-thiosemicarbazones are found in the literature as substances with great biological potential, such as antibacterial, antitumor, antifungal, among others. However, there are several procedures by which isatin and thiosemicarbazones are combined to synthesize the desired hybrid products. In this work, 18 (eighteen) precursors 4-X-phenyl-thiosemicarbazones and 3-X- phenyl-thiosemicarbazones with different substituents on the aromatic ring were synthesized, where X =H, Cl, Br, F, OCH3, N(CH3)2, OH, CF3, CH3, NO2. Subsequently, 18 (eighteen) new hybrid derivatives were obtained through the reaction of these thiosemicarbazones with isatin. All compounds were properly characterized through routine spectroscopic techniques, the thiosemicarbazones only with IR, as their structures are described in the literature, and the final products were unpublished through the techniques of IR, 1H and 13C NMR. Isatin-thiosemicarbazones were tested for antifungal activity, using the Radial Growth techniques with Aspergillus parasiticus and Minimum Inhibitory Growth (MIC) with Sporothrix schenkii, showing very satisfactory results. The investigation of the structure-activity correlation was carried out using data from the electronic and hydrophobic effects of the synthesized molecules. Finally, the final products were investigated for their chelating effect with iron (II) ions.