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• A series of novel steroidal β-triazoly enones were designed and prepared as anticancer compounds. • Compound 5a inhibited PC-3 and MGC-803 cells potently (IC 50 = 1.61 and 1.16 μM, respectively). • Compound 5a was less toxic toward GES-1 with an IC 50 of 20.72 μM. • Compound 5a inhibited migration and invasion of MGC-803 and PC-3 cells. • Compound 5a treatment caused changes of mRNA levels and protein expression of EMT markers in MGC-803 and PC-3 cells. β-Triazoly enones are biologically interesting scaffolds, incorporation of such scaffolds into the steroid nucleus may generate new bioactive steroids and further enrich structural types of steroids. In this work, a series of new steroidal β -triazoly enones were synthesized based on click chemistry and Claisen–Schmidt condensation reaction and further evaluated for their antiproliferative activity against a panel of cancer cells. Most of these compounds showed better potency against PC-3 and MGC-803 cells. Particularly, compound 5a inhibited PC-3 and MGC-803 cells potently with the IC 50 values of 1.61 and 1.16 μM, respectively, and was less toxic toward GES-1 with an IC 50 value of 20.72 μM. Further mechanistic studies showed that compound 5a inhibited migration and invasion of MGC-803 and PC-3 dose-dependently. Treatment with compound 5a varied mRNA levels and protein expression of EMT markers in both cells. Collectively, the steroidal β -triazoly enones could be potentially utilized to develop new anticancer agents with the ability of inhibiting cell migration and invasion. [ABSTRACT FROM AUTHOR]