1178892-65-3Relevant academic research and scientific papers
Synthesis of a Coumarin-Based Analogue of Schweinfurthin F
Beutler, John A.,Dey, Patrick N.,Schroeder, Chloe M.,Wiemer, David F.
, p. 16824 - 16833 (2021/11/16)
The natural schweinfurthins are stilbenes with significant antiproliferative activity and an uncertain mechanism of action. To obtain a fluorescent analogue with minimal deviation from the natural structure, a coumarin ring system was annulated to the D-ring, creating a new analogue of schweinfurthin F. This stilbene was prepared through a convergent synthesis, with a Horner-Wadsworth-Emmons condensation employed to form the central stilbene olefin. After preparation of a tricyclic phosphonate via a recent and more efficient modification of the classic Arbuzov reaction, condensation was attempted with an appropriately substituted bicyclic aldehyde but the coumarin system did not survive the reaction conditions. When olefin formation preceded generation of the coumarin, the stilbene formation proceeded smoothly and ultimately allowed access to the targeted coumarin-based schweinfurthin analogue. This analogue displayed the desired fluorescence properties along with significant biological activity in the National Cancer Institute’s 60-cell line bioassay, and the pattern of this biological activity mirrored that of the natural product schweinfurthin F. This approach gives facile access to new fluorescent analogues of the natural schweinfurthins and should be applicable to other natural stilbenes as well.
Total syntheses of graphisin A and sydowinin B
Little, Andrew,Porco, John A.
supporting information; experimental part, p. 2862 - 2865 (2012/07/17)
Efficient syntheses of the highly substituted benzophenone graphisin A and the xanthone sydowinin B are described. Key steps involve aryl anion addition to substituted benzaldehyde derivatives, subsequent methyl ester installation, and dehydrative cycliza
Synthesis and biological activity of a fluorescent schweinfurthin analogue
Kuder, Craig H.,Neighbors, Jeffrey D.,Hohl, Raymond J.,Wiemer, David F.
experimental part, p. 4718 - 4723 (2009/12/01)
Most of the natural schweinfurthins are potent and selective inhibitors of cell growth as measured by the National Cancer Institute's 60-cell line screen. Due to the limited supply of these natural products, we have initiated a program aimed at their synt
SCHWEINFURTHIN ANALOGUES
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Page/Page column 28, (2010/01/30)
The invention provides fluorescent schweinfurthin analogs of formula(I) which are useful as probes and for the treatment of cancer and other diseases.
