Synthesis and cytotoxicity of diastereomeric benzylamides derived from maslinic acid, augustic acid and bredemolic acid

36 substituted benzylamides were prepared starting from maslinic acid, bredemolic acid, and augustic acid and evaluated for their cytotoxicity in SRB assays employing several human tumor cell lines as well as non-malignant fibroblasts. Thereby, the benzylamides of maslinic acid, however, were found to be more cytotoxic than those obtained from augustic acid or bredemolic acid. The best compound (18, derived from maslinic acid) showed an EC50 value of 1.3 mu M against A375 melanoma cells. Additional staining experiments revealed that this compound acted rather by apoptosis than by necrosis.

Automated summary

36 substituted benzylamides were synthesized from maslinic acid, bredemolic acid, and augustic acid, and their cytotoxicity was evaluated in various human tumor cell lines and non-malignant fibroblasts. The benzylamides derived from maslinic acid exhibited higher cytotoxicity compared to those derived from augustic acid or bredemolic acid. The most effective compound (compound 18, derived from maslinic acid) showed an EC50 value of 1.3 μM against A375 melanoma cells. Further staining experiments revealed that this compound primarily induced apoptosis rather than necrosis.