Syntheses and cytotoxicities of the analogues of the taxoid brevifoliol

Seven novel brevifoliol analogues have been synthesized by coupling brevifoliol and 2-monosubstituted-4-phenyl-1,3-oxazolidine carboxylic acid after removal of the protecting group with acid treatment. Brevifoliol and its synthesized analogues were tested for their cytotoxic activities against four different human cancer cell lines, oral (KB), breast (MCF-7), colon (CaCO2) and liver (HepG-2) as determined by MTT assay. The C-13 oxidized brevifoliol retained significant activity. Out of the seven analogues synthesized, C-13 oxidized brevifoliol-5-[N-tert-butoxycarbonyl amino-(2′R,3′S)-3′-phenyl isoserine] analogue was interesting as it exhibited selective and potent cytotoxicity against liver cancer cell line predominantly.

Graphical abstractThe chemical modifications of the taxoid brevifoliol led to seven analogues, some of which possessed selective and potent cytotoxicity.Figure optionsDownload full-size imageDownload as PowerPoint slide