This study aimed to synthesize, characterize, and evaluate the antioxidant and anticancer activities of 18 novel carbazole derivatives with thiosemicarbazide functional groups. The compounds were assessed for their radical scavenging capabilities using the 2,2-diphenyl-1-picrylhydrazyl assay and their antiproliferative effects on MCF-7 cancer cells through viability assays. Additionally, the modulation of the PI3K/Akt/mTOR pathway, apoptosis/necrosis induction, and cell cycle analysis were conducted for the most promising anticancer agents. Nine compounds showed potent antioxidant activities, with IC50 values lower than the positive control acarbose, and compounds 4h and 4y exhibited the highest potency (IC50 values of 0.73 and 0.38 μM, respectively). Compounds 4o and 4r displayed significant anticancer effects, with IC50 values of 2.02 and 4.99 μM, respectively. Compound 4o particularly showed promising activity by targeting the PI3K/Akt/mTOR signaling pathway, inhibiting tumor survival, inducing apoptosis, and causing cell cycle arrest in MCF-7 cell lines. It also demonstrated significant antimicrobial activities against *Staphylococcus aureus* and *Escherichia coli*, and antifungal effects against *Candida albicans*. Molecular docking simulations supported these findings, revealing favorable binding profiles and interactions within the active sites of the enzymes PI3K, AKT1, and mTOR. The druggability of the newly synthesized thiosemicarbazide derivatives was assessed, showing optimal physicochemical properties, further endorsing their potential as drug candidates.This study aimed to synthesize, characterize, and evaluate the antioxidant and anticancer activities of 18 novel carbazole derivatives with thiosemicarbazide functional groups. The compounds were assessed for their radical scavenging capabilities using the 2,2-diphenyl-1-picrylhydrazyl assay and their antiproliferative effects on MCF-7 cancer cells through viability assays. Additionally, the modulation of the PI3K/Akt/mTOR pathway, apoptosis/necrosis induction, and cell cycle analysis were conducted for the most promising anticancer agents. Nine compounds showed potent antioxidant activities, with IC50 values lower than the positive control acarbose, and compounds 4h and 4y exhibited the highest potency (IC50 values of 0.73 and 0.38 μM, respectively). Compounds 4o and 4r displayed significant anticancer effects, with IC50 values of 2.02 and 4.99 μM, respectively. Compound 4o particularly showed promising activity by targeting the PI3K/Akt/mTOR signaling pathway, inhibiting tumor survival, inducing apoptosis, and causing cell cycle arrest in MCF-7 cell lines. It also demonstrated significant antimicrobial activities against *Staphylococcus aureus* and *Escherichia coli*, and antifungal effects against *Candida albicans*. Molecular docking simulations supported these findings, revealing favorable binding profiles and interactions within the active sites of the enzymes PI3K, AKT1, and mTOR. The druggability of the newly synthesized thiosemicarbazide derivatives was assessed, showing optimal physicochemical properties, further endorsing their potential as drug candidates.