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US 8,946,287 B2Granted
Chemotherapeutic flavonoids, and syntheses thereof
AssigneePurdue Research Foundation
InventorsMark S. Cushman, John M. Pezzuto, Arup Mati
Life of this patent
Estimating the term…
Abstract
Substituted flavonoid compounds, and pharmaceutical formulations of flavonoid compounds are described. Also described are processes for preparing flavonid compounds, as are methods for treating cancer in mammals using the described flavonoid compounds or pharmaceutical formulations thereof.
Claims10
A compound of the formula
- and pharmaceutically acceptable salts thereof, wherein:
- bond a is a single bond;
- Ra represents 2-4 substituents where at least 2 of said substituents are adjacent substituents and are taken together to form alkylenedioxy, and where any remaining substituents are each independently selected from the group consisting of halo, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, cyano, nitro, optionally substituted alkylthio, optionally substituted alkylsulfonyl, carboxylic acid and derivatives thereof, and sulfonic acid and derivatives thereof;
- and
- Rc represents 1-4 substituents each of which is independently selected from the group consisting of halo, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, cyano, nitro, optionally substituted alkylthio, optionally substituted alkylsulfonyl;
- carboxylic acid and derivatives thereof, and sulfonic acid and derivatives thereof;
- provided that at least one of Rc is alkenyl;
- and
- provided that when Ra is 7-hydroxy and alkylenedioxy or 7-alkoxy and alkylenedioxy, Rc is not 4′-hydroxy or 4′-alkoxy.
6 more elements
A process for preparing a compound of the formula
- from an enone intermediate, the process comprising:
- reacting a compound of the formula
- with a compound of the formula
- and
- cyclizing the enone intermediate, wherein:
- Ra represents 2-4 substituents where at least 2 of said substituents are adjacent substituents and are taken together with the attached carbons to form alkylenedioxy, and where any remaining substituents are each independently selected from the group consisting of halo, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, cyano, nitro, optionally substituted alkylthio, optionally substituted alkylsulfonyl, carboxylic acid and derivatives thereof, and sulfonic acid and derivatives thereof;
- and
- group consisting of halo, hydroxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkoxy, cyano, nitro, optionally substituted alkylthio, optionally substituted alkylsulfonyl, carboxylic acid and derivatives thereof, and sulfonic acid and derivatives thereof;
- provided that at least one of Rc is alkenyl;
- and
- provided that when Ra is 7-hydroxy and alkylenedioxy or 7-alkoxy and alkylenedioxy, Rc is not-4′-hydroxy or 4′-alkoxy.
8 more elements
Dependencies are inferred from the claim text.