Synthesis and cytotoxic activity of fluorinated analogues of Goniothalamus lactones. Impact of fluorine on oxidative processes

Novel fluorinated analogues of goniothalamin 1 and howiinol A 2 have been prepared from trifluorocrotonate derivatives. Trifluoromethyl goniothalamin (R/S) 4 showed a slightly lower activity than 1, while the trifluoromethyl howiinol A 16 exhibited similar activities on several cell lines in the micromolar range. Unlike (R) goniothalamin and howiinol A, trifluoromethyl parent compounds remained unchanged when submitted to biomimetic oxidative systems.

Graphical abstractNovel trifluoromethyl analogues of goniothalamin and howiinol A have been prepared and exhibited slightly lower or similar cytotoxicity towards various cancer cell lines. The CF3 group prevented from biomimetic oxidative processes all sites of molecules 4 and 16.Figure optionsDownload full-size imageDownload as PowerPoint slide