Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular docking studies of new imidazolyl hydrazone derivatives


Tapera M., Kekeçmuhammed H., TÜZÜN B., SARIPINAR E., KOÇYİĞİT Ü. M., Yıldırım E., ...More

Journal of Molecular Structure, vol.1269, 2022 (SCI-Expanded) identifier

  • Publication Type: Article / Article
  • Volume: 1269
  • Publication Date: 2022
  • Doi Number: 10.1016/j.molstruc.2022.133816
  • Journal Name: Journal of Molecular Structure
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, INSPEC
  • Keywords: Cytotoxic activity, Enzyme inhibition, Hydrazone, Imidazole, Synthesis
  • Kocaeli University Affiliated: No

Abstract

© 2022 Elsevier B.V.A new series of imidazolyl hydrazone derivatives IA (1-12) were prepared from a condensation reaction between indoline-2,3-dione (isatin) and 2-benzylidenehydrazinecarboximidamide derivatives. The structure of compounds was elucidated using various spectral techniques including FTIR, 1H NMR, 13C NMR, and HRMS. The proposed structure of IA-2 was determined by single-crystal X-ray analysis. Synthesized compounds were evaluated for their inhibitory action against carbonic anhydrase I and II isoenzymes (hCA I and hCA II), as well as cytotoxicity activity in a cancer cell line (HT-29) and a healthy cell line (NIH 3T3). Among them, some compounds exhibited remarkable CA inhibitory activities compared to a standard inhibitor with Ki values in the range of 13.434 ± 3.278-522.549 ± 360.720 nM for hCA I (Ki value for standard inhibitor = 271.15 ± 74.620 nM) and 41.108 ± 10.180-271.171 ± 65.293 nM for hCA II (Ki value for standard inhibitor = 113.07 ± 20.980 nM) and significant antiproliferative activity with less toxicity to a health cell line. In addition, the theoretical parameters of the bioactive molecules were calculated to establish their drug-likeness qualities and ADME/T analysis was carried out to examine the drug properties of the synthesized compounds.