Schiff bases from the thiosemicarbazones family with variable N4 substituents are known to show enhanced growth inhibitory properties. In view of these facts and as a part of our continuous interest in cationic Schiff bases, we have developed several Schiff base ligands from (3-formyl-4-hydroxyphenyl) methyltriphenylphosphonium (T) in present study. The compounds were characterized by various spectroscopic methods (infrared spectra, H-1 NMR, C-13 NMR, HRESIMS and X-ray crystallography). Three of the N4 substituents, namely P(tsc)T, FP(tsc)T and EP(tsc)T exerted strong growth inhibitory properties by inhibiting the highly metastasis prostate cancer growth (PC-3). The thiosemicarbazone with ethyl-phenyl (EP) moiety displayed most potent activity against all cell lines tested. The MIT data obtained from analysis establishes that phenyl substituent enhances the growth inhibitory properties of the compound. The result affirms that EP(tsc)T would serve as a lead scaffold for rational anticancer agent development. (C) 2017 Elsevier B.V. All rights reserved.