This scholarly investigation presents pioneering drug candidates for combating leukemia, distinguished by reduced side effects and elevated efficacy. The study focuses on azo compounds for their selective targeting against cancerous cells and customizable properties. Novel azo compounds, DMTPC and DMTPD, were skillfully synthesized via diazotization of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline with dimedone and meldrum‘s acid. Comprehensive characterization employed advanced analytical techniques like 1H-NMR, 13C-NMR, LC-MS, FT-IR, and XRD. UV-Vis and fluorescence spectro photometers scrutinized absorption and fluorescence properties in diverse solvents. Theoretical DFT computations provided optimized geometries, vibrational frequencies, NMR chemical shifts, absorption wavelengths, HOMOs-LUMOs, Mulliken charges, and molecular orbital energies. Encouragingly, experimental and theoretical values aligned well. ADME properties and toxicity profiles were evaluated using online web servers. Molecular dynamics simulations explored interactions of DMTPC and DMTPD with the leukemia inhibitory factor protein (PDB ID:1EMR) compared to Nilotinib. Molecular docking studies indicated DMTPC’s promising potential with a binding energy of 8.8 kcal/mol, approaching Nilotinib’s 9.4 kcal/mol. This investigation accentuates the burgeoning research paradigm of exploiting azo compounds in the formidable battle against leukemia, opening new avenues for breakthroughs in this field.