Platanic acid: A new scaffold for the synthesis of cytotoxic agents.

Thirty-seven different derivatives (2-38) have been prepared from platanic acid, a natural occurring triterpenoid. Main emphasis was the introduction of several N-containing functional groups such as amines, amides and oximes and their screening for cytotoxic activity employing several human tumor cell lines using SRB assays. In these SRB assays, nearly all compounds showed good cytotoxicity for these human tumor cell lines. Two compounds (17 and 38), however, were submitted to extended biological testing and investigated with respect to their mode of action using fluorescence microscopy and FACS analysis. Compound 17, a methyl (3β, 20R) 3-acetyloxy-20-amino-30-norlupan-28-oate, induced apoptosis in A2780 ovarian carcinoma cells.