Synthesis, Characterization, Antioxidant Evaluation, Cytotoxicity Studies, and Molecular Docking of Novel Sulfonamide Derivatives
Journal of Biochemical and Molecular Toxicology, cilt.40, sa.7, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 40 Sayı: 7
- Basım Tarihi: 2026
- Doi Numarası: 10.1002/jbt.70981
- Dergi Adı: Journal of Biochemical and Molecular Toxicology
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, BIOSIS, Chemical Abstracts Core, EMBASE, Environment Index, MEDLINE, Zoological Record, Natural Science Collection (ProQuest), Biological Science Database (ProQuest), Biomedical Reference Collection: Corporate Edition (EBSCO), Health Research Premium Collection (ProQuest)
- Anahtar Kelimeler: A2780, antioxidant activity, cytotoxicity, DPPH assay, LNCaP, molecular docking, MTT assay, Schiff base, sulfonamide derivatives
- İnönü Üniversitesi Adresli: Evet
Özet
A series of novel sulfonamide derivatives (4a–i) was synthesized via a three-step sequence involving Schiff base formation, sodium borohydride reduction to the corresponding secondary amines (2a–i), and subsequent treatment with p-toluenesulfonyl chloride in the presence of sodium carbonate. The structures of all intermediates and final products were unambiguously confirmed by FT-IR, 1H NMR, 13C NMR, and HRMS analyses. The antioxidant activity of the target compounds was assessed using the DPPH radical scavenging assay with BHT as a reference standard. Among the synthesized derivatives, compound 4d exhibited the most pronounced antioxidant activity, surpassing BHT at concentrations of 37.5 and 62.5 µg/mL. The cytotoxicity of the compounds was evaluated against human ovarian carcinoma (A2780) and prostate cancer (LNCaP) cell lines using the MTT assay, with docetaxel as a positive control. Compounds 4g, 4h, and 4i demonstrated the highest cytotoxic potency against both cell lines, with compound 4h displaying a log IC50 value of 1.343 µg/mL against LNCaP cells. Structure–activity relationship analysis suggests that the methoxy substituent enhances cytotoxic activity, likely through increased lipophilicity and electron-donating effects facilitating interactions with biological targets. Molecular docking studies were performed to further rationalize the observed biological activities.