Polar substituted Schiff bases and 1,2,3-triazole hybrids 2 - 6 were successfully synthesized by Schiff base condensation reaction between pre-prepared triazole 1 and series of polar substituted amines. The chemical structures of the hybrids were confirmed using spectroscopies (NMR and FTIR), CHN-elemental analysis and single crystal X-ray diffraction analysis. The compounds were evaluated for their antiproliferative activity against two cancer cells: PC3 (prostate) and MCF7 (breast) cell lines using Alamarblue assay method and Camptothecin was employed as a standard. All the compounds exhibited good activity for the proliferation of the cancer cell lines compared to the standard and their activity is concentration dependent. Compounds 1, 2, 4 and 5 exhibited good caspase activity with relevant dosages that inhibited 50% (IC50) in prostate cancer cell. All the compounds exhibited high binding affinity for Human 3-alpha hydroxysteroid dehydrogenase type 3 (pdb id: 4xo6) and Androgen receptor (pdb id: 2Q7K) inhibitors compared to the reference anticancer drug (Camptothecin). Structure activity relationships (SARs) of the tested compounds is in good agreement with DFT and molecular docking studies. ADMET analysis was used to predict the pharmacokinetics, pharmacodynamics and toxicology study of the compounds and proved that the compounds exhibited desirable physicochemical properties for drug likeness.