Novel Carbazole-Acylthiourea Derivatives: Synthesis, Antimicrobial, Antioxidant, Hemocompatibility, Cytotoxicity, and ADME-Tox Profiling.

Authors

Carmen Limban, Ioana Cristina Marinaş, Mariana Carmen Chifiriuc, Miron Teodor Căproiu, Florea Dumitraşcu, Erzsébet-Eleonóra Kapronczai, Irina Zarafu, Diana Camelia Nuţă, Petre Ioniţă, Speranţa Avram, Cătălina Mareş, Andra Maria Păun, Bogdan Mihai Cristea, Carmellina Daniela Bădiceanu, Ilinca Margareta Vlad, Maria Coandă, Delia Laura Popescu, Coralia Bleotu

Published in

ChemistryOpen. Volume 15. Issue 11. Pages e70258.

Abstract

A focused series of four carprofen-derived carbazole-acylthiourea N-(arylcarbamothioyl)propanamides (1a-d) was synthesized by in situ generation of 2-(6-chloro-9H-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.

PMID:
42862714
Bibliographic data and abstract were imported from PubMed on 13 Oct 2026.

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