Synthesis, characterization and investigation of cytotoxic effects of novel N-phenylbenzene-1,2-diamine ligands against different cancer cell lines

Schiff bases are important compounds formed by the condensation reaction between primary amines and aldehydes and have a wide range of therapeutic applications. Their privileged chemical structure and diversity of biological activities enable the use of various derivatives of Schiff bases as potential anticancer agents and the development of promising new treatment strategies in this field. This thesis aimed to synthesize and characterize various Schiff bases by reaction of N1-phenylbenzene-1,2-diamine with different aldehydes and to determine the effects of these molecules against cancer cells. 1H NMR, 13C NMR and FTIR spectra of five new and one commercial compounds were characterized and their antiproliferative effects were evaluated against DLD-1 (colorectal), MCF-7 (breast) and A549 (lung) cancer cell lines. According to the findings, the synthesized Schiff base ligands SN-194 [(E)-2,4-dibromo-6-(((2-(phenylamino)phenyl)imino)methyl)phenol], SN-193 [(E)-2-chloro-4-fluoro-6-(((2-(phenylamino)phenyl)imino)methyl)phenol], The activity levels of SN-208 [(E)-4-bromo-2-(((2-(phenylamino)phenyl)imino)methyl)phenol] and SN-197 [(E)-2-methyl-6-(((2-(phenylamino)phenyl)imino)methyl)phenol] varied in different cell lines and the synthesized compounds were especially effective against MCF-7 cell line compared to other cell lines. SN-194 exhibited the strongest antiproliferative effect with the lowest IC50 values in all cell lines. In particular, it showed a more effective activity against DLD-1 cells (3.096 µM) than the reference drug sorafenib (6.578 µM), indicating that it may be the most suitable candidate for evaluation in anticancer drug development studies in related cells.