Semisynthetic derivatives of sesquiterpene lactones by palladium-catalyzed arylation of the alpha-methylene-gamma-lactone substructure.
The palladium-catalyzed arylation of different alpha-methylene-gamma-lactone-containing sesquiterpene lactones was shown to produce E-olefin coupling products selectively in moderate to excellent yields. Biological evaluation of these semisynthetic sesquiterpene lactone derivatives in HeLa cells showed interesting antiproliferative profiles and provided initial structure-activity data.
Han
Changho
C
Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, USA.
Barrios
Francis J
FJ
Riofski
Mark V
MV
Colby
David A
DA
D000475:Alkenes / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D002384:Catalysis; D006367:HeLa Cells / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D012717:Sesquiterpenes / Q000138:chemical synthesis / Q000494:pharmacology; D013329:Structure-Activity Relationship
D000475:Alkenes; D000970:Antineoplastic Agents; D007783:Lactones; D012717:Sesquiterpenes; C416683:methylene-lactone; D010165:Palladium