<p>The synthesis and investigation of 2-cyano-N’-(2-hydroxybenzylidene)-3-phenylacrylohydrazide (H₂L) and its Ni²⁺, Cu²⁺, Co²⁺ and Zn²⁺ complexes are discussed in this paper. These compounds were characterized with different techniques, including CHN, IR, MS, ¹³C &amp; ¹HNMR, TGA, ESR, UV-Visible and the magnetic moments. DFT calculations (DFT/B3LYP) level was used for geometry optimization of the suggested structures with 6-311 + + G(d, p) basis set. An octahedral stereochemistry was suggested for Ni²⁺ and Co²⁺ complexes while; a square planar geometry was proposed for Cu²⁺complex. The results proposed four coordinated stereochemistry for Zn²⁺ complex. The IR spectra of the H₂L were simulated and compared with the experimental result, achieving a correlation coefficient R² = 0.99976. The UV-visible spectra were used in determining the optical band gaps and found to be in the range 3.26–3.28&#xa0;eV. Non-linear optical (NLO) properties of the DFT optimized compounds were investigated and indicated higher values in comparison with urea. The molecular docking was utilized to study the possible interactions between the synthesized compounds and the targeted proteins of liver and colon cancer. The suggested compounds were examined towards HeP2G and HCT-116 cell lines to determine their anticancer activity that are compared to Doxorubicin and Sorafenib as standards. H₂L exhibited strong cytotoxicity against HeP2G cell line; on the other hand, Zn²⁺ complex exhibited strong cytotoxicity against HCT-116 cell line.</p>