A series of novel N,N-cyclic-2,4-dihydroxythiobenzamide derivatives is described. Test compounds were formed by the reaction of the commercially available reagents with sulfinylbis[(2,4-dihydroxyphenyl)methanethione] (STB). The chemical structures were confirmed by IR, 1H NMR, 13CNMR, EI-MS, and elemental analysis. For the estimation of potential activity in vitro, the MIC values against strains of Candida were determined. Antifungal properties of selected compounds under in vitro conditions against five phytopathogenic fungi were estimated. Furthermore, the antiproliferative activity against the HCV29T cancer cell lines has been studied. These compounds exhibited antiproliferative activity in the range of 33.98-10.51 µg/mL.