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.
Dumitrescu
Lidia
L
UMR-CNRS 8076, Molécules fluorées et chimie médicinale, IFR 141, Faculté de Pharmacie, Université Paris-Sud, J. B. Clément, 5, rue Jean-Baptiste Clement, 92290 Châtenay-Malabry, France.
Mai Huong
Doan Thi
DT
Van Hung
Nguyen
N
Crousse
Benoit
B
Bonnet-Delpon
Danièle
D
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D045744:Cell Line, Tumor; D005461:Fluorine / Q000737:chemistry*; D054335:Goniothalamus / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry*; D010084:Oxidation-Reduction; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000970:Antineoplastic Agents; D007783:Lactones; D011753:Pyrones; C426486:howiinol A; D005461:Fluorine; C103280:goniothalamin