Synthesis of Sulfonamide‐Based Schiff Bases as Potent Anticancer Agents: Spectral Analyses, Biological Activity, Molecular Docking, ADME, DFT, and Pharmacophore Modelling Studies


Başaran E., Çakmak R., Türkmenoğlu B., Akkoc S., Köprü S.

CHEMISTRY AND BIODIVERSITY, cilt.21, ss.1-17, 2024 (SCI-Expanded) identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 21
  • Basım Tarihi: 2024
  • Doi Numarası: 10.1002/cbdv.202402229
  • Dergi Adı: CHEMISTRY AND BIODIVERSITY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Agricultural & Environmental Science Database, Aquatic Science & Fisheries Abstracts (ASFA), CAB Abstracts, Chemical Abstracts Core, EMBASE, MEDLINE, Veterinary Science Database
  • Sayfa Sayıları: ss.1-17
  • Erzincan Binali Yıldırım Üniversitesi Adresli: Evet

Özet

The current study focuses on the synthesis and characterization of six benzenesulfonamide‐based Schiff base derivatives (7–12) with various electron‐withdrawing and electron‐donating substituents (‐F, ‐CI, ‐Br, ‐CH3, and ‐OCH3) and the assessment of their antiproliferative activities against human lung (A549) and liver (HepG2) cancer cell lines using in vitro and in silico approaches. The structures of the synthesized compounds (7–12) were elucidated by elemental analysis and FT‐IR, 1D (1H, 13C, APT, and DEPT‐135), and 2D (HMQC and HMBC) NMR spectroscopies. The cytotoxic activities of the targeted compounds were determined at various concentrations against these cancer cell lines for 72 h, using the MTT method. The targeted molecules (7–12) demonstrated remarkable antiproliferative activities, with IC50 values ranging from 6.032–9.533 μM against the A549 cell line and 5.244–9.629 μM against the HepG2 cell line. These compounds showed activities at lower or very similar concentrations to cisplatin against the A549 cell line and at much lower concentrations than cisplatin against the HepG2 cell line. Among them, compounds 10 and 12 were found to be more effective against A549 and HepG2 cells, respectively, than cisplatin. These compounds were analyzed by interacting with the 1BNA, 4HJO, and 4ASD crystal structures in molecular docking studies.