Synthesis, structural characterisation and biological evaluation of fluorinated analogues of resveratrol.
Resveratrol is a potential chemopreventive agent and can be isolated from grape skins and other dietary sources. The Wittig reaction and the decarbonylative Heck reaction were employed to synthesise analogues of this stilbene. Fluorinated derivatives of this stilbene were synthesised maintaining the 3,4',5-substitution pattern. The hydroxyl groups were also replaced by amino groups and the biological activity evaluated. The compounds were assayed on a variety of cell lines, primarily the non-small lung carcinoma cell line DLKP-A. Analogues were evaluated alone and in combination with a known chemotherapeutic agent epirubicin.
Moran
Brian W
BW
School of Chemical Sciences, Dublin City University, Glasnevin, Dublin 9, Ireland.
Anderson
Frankie P
FP
Devery
Aoife
A
Cloonan
Stephen
S
Butler
William E
WE
Varughese
Sunil
S
Draper
Sylvia M
SM
Kenny
Peter T M
PT
D000903:Antibiotics, Antineoplastic / Q000494:pharmacology / Q000627:therapeutic use; D016588:Anticarcinogenic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D015251:Epirubicin / Q000494:pharmacology / Q000627:therapeutic use; D054879:Halogenation; D006801:Humans; D015394:Molecular Structure; D009369:Neoplasms / Q000188:drug therapy; D000077185:Resveratrol; D013267:Stilbenes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology* / Q000627:therapeutic use; D013329:Structure-Activity Relationship
D000903:Antibiotics, Antineoplastic; D016588:Anticarcinogenic Agents; D013267:Stilbenes; D015251:Epirubicin; D000077185:Resveratrol