Synthesis, characterization and molecular docking studies of highly selective new hydrazone derivatives of anthranilic acid and their ring closure analogue Quinazolin-4(3H)-ones against lung cancer cells A549

Tokali F. S., ŞENOL H., Bulut S., HACIOSMANOĞLU E.

JOURNAL OF MOLECULAR STRUCTURE, cilt.1282, 2023 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 1282
  • Basım Tarihi: 2023
  • Doi Numarası: 10.1016/j.molstruc.2023.135176
  • Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, Chimica, Compendex, INSPEC
  • İstanbul Üniversitesi-Cerrahpaşa Adresli: Hayır

Özet

In this study, new Schiff bases derived from anthranilic acid hydrazide (3a-j) and quinazolin-4(3H)-one (4a-j) were synthesized with high yields (99-90%) and characterized by FTIR, NMR ( 1 H and 13 C), and HRMS spectroscopic techniques. The effects of the synthesized compounds on the human lung adeno-carcinoma cells (A549, CCL-185, ATCC) and the human bronchial epithelial cells (BEAS-2B, ECACC) were examined. IC50 values of the compounds were found in the range of 12.40 - 424.9 mu M against A549 and 15.81 - 752.30 mu M against BEAS-2B cell lines. Compounds 3i, 3j, 4b , and 4f are the most active com-pounds in the series, with low IC50 values against A549, high against BEAS-2B, and high selectivity. For the most active compounds in the series, molecular docking study was performed to understand ligand-protein interactions between the compounds and Epidermal Growth Factor Receptor (EGFR) and Vascular Endothelial Growth Factor Receptor (VEGFR1). The docking scores were calculated in the range of-5.870 --6.711 kcal/mol for EGFR and-4.142 --8.501 kcal/mol for VEGFR1. (c) 2023 Elsevier B.V. All rights reserved.