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

Lidia Dumitrescu; Doan Thi Mai Huong; Nguyen Van Hung; Benoit Crousse; Danièle Bonnet-Delpon

doi:10.1016/j.ejmech.2010.03.032

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

Eur J Med Chem. 2010 Jul;45(7):3213-8. doi: 10.1016/j.ejmech.2010.03.032. Epub 2010 Mar 25.

Authors

Lidia Dumitrescu¹, Doan Thi Mai Huong, Nguyen Van Hung, Benoit Crousse, Danièle Bonnet-Delpon

Affiliation

¹ 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.

PMID: 20392543
DOI: 10.1016/j.ejmech.2010.03.032

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology
Cell Line, Tumor
Fluorine / chemistry*
Goniothalamus / chemistry*
Humans
Inhibitory Concentration 50
Lactones / chemistry*
Oxidation-Reduction
Pyrones / chemical synthesis
Pyrones / chemistry*
Pyrones / pharmacology*
Structure-Activity Relationship

Substances

Antineoplastic Agents
Lactones
Pyrones
howiinol A
Fluorine
goniothalamin