A series of novel 1,2,4-triazolo [3,4-a] phthalazine derivatives were synthesized in five steps from a common precursor, phthalic anhydride. Most of synthesized phthalazine derivatives showed inhibitory activity against Staphylococcus aureus. One of phthalazine derivatives 5l showed inhibitory activity against all tested bacterial and fungal strains.

•A new class of steroidal pyran–oxindole hybrids were efficiently synthesized in one pot.•These compounds were more sensitive to MCF-7 and MGC-803 cells.•Compounds 4f and 4i were more potent than 5-Fu against T24 and MGC-803 cells.•Compound 4f showed excellent cytotoxicity against T24 cells (IC50 = 4.43 μM).•Compound 4i showed cell cycle arrest at G2/M phase and induced early apoptosis.A series of novel steroidal pyran–oxindole hybrids were efficiently synthesized in a single operation through the vinylogous aldol reaction of vinyl malononitrile 3 with substituted isatins involving the construction of C–C and C–O bonds. Some compounds displayed moderate to good cytotoxicity against T24, SMMC-7721, MCF-7 and MGC-803 cells. Compounds 4f and 4i were more potent than 5-Fu against T24 and MGC-803 cells with the IC50 values of 4.43 and 8.45 μM, respectively. Further mechanism studies indicated that compound 4i induced G2/M arrest and early apoptosis in a concentration- and time-dependent manner.Graphical abstractDownload full-size image