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In the current work, new 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine derivatives (1–8) were synthesized via the ring closure reaction of 2-bromoacetophenone derivatives with 4-amino-5-[(5-methoxy-2-methyl-1-(4-chlorobenzoyl)-1H-indol-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, which was obtained via the solvent-free reaction of indomethacin with thiocarbohydrazide. MTT assay was carried out to determine the cytotoxic effects of the compounds on T98 human glioma cell line. Among these compounds, 3-[5-methoxy-2-methyl-1-(4-chlorobenzoyl)-1H-indole-3-yl)methyl]-6-(4-methylphenyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine (8) was found to be the most effective compound and therefore flow cytometric method was performed to investigate the apoptotic effect of compound 8. The apoptosis stimulating percentages of compound 8 in comparison with the control group at 50 and 100 μM doses were calculated …