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In this paper, we present the synthesis, characterization and evaluation of antiproliferative activity for four compounds carrying the 4-amino-5-mercapto-1,2,4-triazol-3-yl scaffold. The synthesis of 1,n-bis-(4-amino-5-mercapto-1,2,4-triazol-3-yl) alkanes was carried out using as starting reagents the dihydrazides of oxalic, malonic, succinic and adipic acids, using mercaptoacetic acid dianion as a leaving group, by a one-pot synthesis method implemented in our research group for the synthesis of 3-substituted-5-mercapto-1,2,4-triazoles. The compounds were obtained with modest yields (12–60%) but with good purity and were characterized by elemental analysis, FTIR, ¹H-NMR and ¹³C-NMR spectroscopy. Also, the stability of the synthesized bis-triazoles was investigated under controlled thermal stress in a dynamic oxidative atmosphere. The last part of the study consisted of biological activity evaluation, by evaluating the antiproliferative activity against the A375 line (human malignant melanoma), as well as on viability of the BJ fibroblast cell line, using MTT and LDH assays.