Novel Carbazole–Acylthiourea Derivatives: Synthesis, Antimicrobial, Antioxidant, Hemocompatibility, Cytotoxicity, and ADME‐Tox Profiling

A focused series of four carprofen‐derived carbazole–acylthiourea N ‐(arylcarbamothioyl)propanamides ( 1a–d ) was synthesized by in situ generation of 2‐(6‐chloro‐9 H ‐carbazol‐2‐yl)propanoyl isothiocyanate followed by reaction with aniline, para ‐toluidine, para‐ bromoaniline, and para‐ iodoaniline, respectively. The structures were supported by FT‐IR, NMR, and APCI‐HRMS analyses. The compounds were evaluated against clinically relevant bacterial and fungal strains, complemented by antioxidant assays, hemocompatibility/antihemolysis models, cancer cell viability assays, and in silico drug‐likeness, pharmacokinetic, pharmacogenomic, and toxicity prediction. The biological profile was substituent‐dependent: 1b showed the strongest activity against Staphylococcus aureus (MIC = 0.25 mg/mL), 1a and 1c were the most active against Enterococcus faecalis (MIC = 0.31 mg/mL), while the iodophenyl derivative 1d was the most potent against Candida albicans (MIC = 0.16 mg/mL). Compounds 1b and 1c also inhibited microbial adherence in selected Gram‐positive and fungal models. Compound 1a displayed the most consistent antioxidant activity across antioxidant assays and protected erythrocytes from AAPH‐induced oxidative hemolysis. The cytotoxicity screening revealed increased sensitivity of A‐431 cells, particularly to 1b (IC50 = 13.67 µg/mL). Molecular docking revealed key binding interactions potentially underlying the observed biological activity. Overall, the integrated data identify carbazole–acylthiourea propanamides, especially 1a and 1b , as promising bioactive scaffolds for further optimization as multifunctional compounds.