The presence of a cationic center is not alone decisive for the cytotoxicity of triterpene carboxylic acid amides

[Display omitted] •3-O-Acetyl-ursolic and 3-O-acetyl oleanolic acid derived piperazinylamides were prepared.•These amides hold either a distal NH, NMe, NMe2 or a N-methyl-N-oxide moiety.•Their cytotoxicity was assessed in SRB assays with a panel of human tumor cell lines.•Compounds holding a quaternary distal N-substituent were less cytotoxic.•Highest cytotoxicity was observed for unsubstituted piperazinylamides. 3-O-Acetyl-ursolic acid (2) and 3-O-acetyl oleanolic acid (8) were converted into piperazinylamides holding a distal NH, NMe or a NMe2 group. These compounds as well as the corresponding N-methyl-N-oxides were accessed. Their cytotoxicity was assessed in SRB assays employing a panel of human tumor cell lines and non-malignant fibroblasts (NIH 3T3). As a result, compounds holding a quaternary distal N-substituent were less cytotoxic that those holding a NH-moiety. Hence, the presence of a distal cationic center seems not to be a sufficient criterion for obtaining triterpenoids of high cytotoxicity and selectivity.