7,11-epi-Thyrsiferol: Completion of Its Synthesis, Evaluation of Its Antimitotic Properties, and the Further Development of an SAR Model

We (a) describe the completion of a total synthesis of 7,11-epi-thyrsiferol (4), (b) compare the antimitotic activities of thyrsiferol (2), Δ15,28-dehydrothyrsiferol (3), and 7,11-epi-thyrsiferol (4), (c) evaluate the synergistic behavior of the title compound and colchicine to inhibit cell prolifer...

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Veröffentlicht in:	Journal of organic chemistry 2006-08, Vol.71 (16), p.5936-5941
Hauptverfasser:	Nishiguchi, Gisele A, Graham, John, Bouraoui, A, Jacobs, R. S, Little, R. Daniel
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antimitotic Agents - chemical synthesis Antimitotic Agents - chemistry Antimitotic Agents - pharmacology Chemistry Colchicine - chemistry Colchicine - pharmacology Exact sciences and technology Furans - chemical synthesis Furans - chemistry Furans - pharmacology Models, Biological Models, Molecular Molecular Structure Organic chemistry Pyrans - chemical synthesis Pyrans - chemistry Pyrans - pharmacology Strongylocentrotus purpuratus - cytology Strongylocentrotus purpuratus - drug effects Strongylocentrotus purpuratus - enzymology Structure-Activity Relationship
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Beschreibung
Zusammenfassung:	We (a) describe the completion of a total synthesis of 7,11-epi-thyrsiferol (4), (b) compare the antimitotic activities of thyrsiferol (2), Δ15,28-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.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo060519z