7,11-epi-thyrsiferol: completion of its synthesis, evaluation of its antimitotic properties, and the further development of an SAR model

Gisele A Nishiguchi; John Graham; A Bouraoui; R S Jacobs; R Daniel Little

doi:10.1021/jo060519z

7,11-epi-thyrsiferol: completion of its synthesis, evaluation of its antimitotic properties, and the further development of an SAR model

J Org Chem. 2006 Aug 4;71(16):5936-41. doi: 10.1021/jo060519z.

Authors

Gisele A Nishiguchi¹, John Graham, A Bouraoui, R S Jacobs, R Daniel Little

Affiliation

¹ Department of Chemistry and Biochemistry, University of California, Santa Barbara, Santa Barbara, California 93106, USA.

PMID: 16872175
DOI: 10.1021/jo060519z

Abstract

We (a) describe the completion of a total synthesis of 7,11-epi-thyrsiferol (4), (b) compare the antimitotic activities of thyrsiferol (2), Delta15,28-dehydrothyrsiferol (3), and 7,11-epi-thyrsiferol (4), (c) evaluate the synergistic behavior of the title compound and colchicine to inhibit cell proliferation, and (d) describe the results of conformational searches that provide additional insight concerning the SAR profile of the thyrsiferol family of natural products.

MeSH terms

Animals
Antimitotic Agents / chemical synthesis*
Antimitotic Agents / chemistry
Antimitotic Agents / pharmacology*
Colchicine / chemistry
Colchicine / pharmacology
Furans / chemical synthesis*
Furans / chemistry
Furans / pharmacology*
Models, Biological*
Models, Molecular
Molecular Structure
Pyrans / chemical synthesis*
Pyrans / chemistry
Pyrans / pharmacology*
Strongylocentrotus purpuratus / cytology
Strongylocentrotus purpuratus / drug effects
Strongylocentrotus purpuratus / enzymology
Structure-Activity Relationship

Substances

Antimitotic Agents
Furans
Pyrans
thyrsiferol
Colchicine