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A series of novel symmetrical trans‐bis‐Schiff bases (11a, 11b, 11c, 11d, 11e, 11f, 11g, 11h, 11i, 11j, 11k, 11l, 11m) were designed and prepared as novel anticancer analogues, with the trans‐configuration confirmed by X‐ray diffraction. Preliminary inhibitory effects of these compounds on CML K562 cell growth were investigated, and the potential analogue 11e showed an excellent anti‐leukemia activity (IC50=6.35 μg/mL), which is higher than that of the clinical drug 5‐fluorouracil (IC50=8.48 μg/mL). Complete assignments had been achieved for the title compounds by spectroscopic techniques, and their structure–activity relationships have been studied.