Semisynthetic derivatives of sesquiterpene lactones by palladium-catalyzed arylation of the alpha-methylene-gamma-lactone substructure

Changho Han; Francis J Barrios; Mark V Riofski; David A Colby

doi:10.1021/jo901533e

Semisynthetic derivatives of sesquiterpene lactones by palladium-catalyzed arylation of the alpha-methylene-gamma-lactone substructure

J Org Chem. 2009 Sep 18;74(18):7176-9. doi: 10.1021/jo901533e.

Authors

Changho Han¹, Francis J Barrios, Mark V Riofski, David A Colby

Affiliation

¹ Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907, USA.

PMID: 19697954
DOI: 10.1021/jo901533e

Abstract

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.

Publication types

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

MeSH terms

Alkenes / chemistry
Antineoplastic Agents* / chemical synthesis
Antineoplastic Agents* / pharmacology
Catalysis
HeLa Cells / drug effects
Humans
Inhibitory Concentration 50
Lactones / chemical synthesis
Lactones / chemistry*
Lactones / pharmacology
Palladium / chemistry*
Sesquiterpenes* / chemical synthesis
Sesquiterpenes* / pharmacology
Structure-Activity Relationship

Substances

Alkenes
Antineoplastic Agents
Lactones
Sesquiterpenes
methylene-lactone
Palladium