1H-Benzo[b]benzo[6,7]cyclohepta[1,2-d]furan-9-carboxaldehyde, 2,3,4,4a,5,6,7,12c-octahydro-10,11-dihydroxy-4,4,7,12c-tetramethyl-, (4aS,7R,12cS)-

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CAS: 874292-32-7
MF: C22H28O4
MW: 356.45532
Synonyms: 1H-Benzo[b]benzo[6,7]cyclohepta[1,2-d]furan-9-carboxaldehyde, 2,3,4,4a,5,6,7,12c-octahydro-10,11-dihydroxy-4,4,7,12c-tetramethyl-, (4aS,7R,12cS)-

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Eric M. Ferreira

University of Georgia
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Dennis L. Wright

University of Connecticut
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Co-reporter: Yanzhong Zhang, E. Zachary Oblak, Erin S.D. Bolstad, Amy C. Anderson, Jerry P. Jasinski, Ray J. Butcher, Dennis L. Wright
pp: 6120-6122
Publication Date(Web):24 November 2010
DOI: 10.1016/j.tetlet.2010.09.058
The natural product liphagal has been shown to function as a reasonably potent and selective inhibitor of the key signaling enzyme PI-3Kα. We have been interested in developing an analog class of PI-3K inhibitors based upon this unusual terpenoid natural product. Toward that end, we have evaluated the binding of the natural product to its target protein computationally and formulated a class of simplified analogs based on the structural analysis. Utilizing the cycloadduct derived from tetrabromocyclopropene and furan, we were able to generate a key, versatile scaffold upon which to pursue this analog design.Image for unlabelled figure

Johan M. Winne

Ghent University
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Tadashi Katoh

Tohoku Pharmaceutical University
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