4′-substituted analogues of fisetin and their use in the treatment of cancer
AssigneesStellenbosch University, Jawaharlal Nehru University
InventorsCatherine Hart Kaschula, Rana Pratap Singh, Arpit Dheeraj, Akash Sabarwal
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Abstract
This invention relates to compounds that are 4′-substituted analogues of the flavonol Fisetin. In particular, the invention relates to such compounds wherein the 4′ position on the B-ring is substituted with a ring deactivating group which has a para-Hammett constant greater than zero, and the use of these compounds in the treatment of cancer, including epithelial cancers.
Claims15
A method of treating cancer in a subject in need thereof, the method comprising administering a therapeutically effective amount of the compound of Formula I:
- or a pharmaceutically acceptable salt or solvate thereof, wherein:
- X is a ring deactivating group selected from —SO2F, —SF5, —NO, —SO2NH2, —CF3, —OCF3, —SCF3, —NCS, —SCN, —SO2CF3, —CHO, —CONH2, —SOCH3, —OSO2CH3, —SO2CH3, —CF2CF3, —CH═CHNO2, —COCH3, —SCOCH3, —CO2C2H5, —CO2CH3, —CONHCH3, —SO2C2H5, —COC3H7, —N═NC6H5, —SO2C6H5, and —OSO2C6H5;
- and
- R7, R6, and R5 are independently selected from H, OH, —O(CH2)OR4, and —OR4, provided that at least one of R7, R6, and R5 is OH, —O(CH2)OR4, or —OR4;
- and
- R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 heteroalkyl, C1-C6 aryl, and C1-C6 heteroaryl.
A pharmaceutical composition comprising a compound of Formula I:
- or a pharmaceutically acceptable salt or solvate thereof, and one or more pharmaceutically acceptable vehicles
- wherein:
- X is a ring deactivating group selected from —SO2F, —SF5, —NO, —SO2NH2, —CF3, —OCF3, —SCF3, —NCS, —SCN, —SO2CF3, —CHO, —CONH2, —SOCH3, —OSO2CH3, —SO2CH3, —CF2CF3, —CH═CHNO2, —COCH3, —SCOCH3, —CO2C2H5, —CO2CH3, —CONHCH3, —SO2C2H5, —COC3H7, —N═NC6H5, —SO2C6H5, and —OSO2C6H5;
- and
- R7, R6, and R5 are independently selected from H, OH, —O(CH2)OR4, and —OR4, provided that at least one of R7, R6, and R5 is OH, —O(CH2)OR4, or —OR4;
- and
- R4 is selected from the group consisting of C1-C6 alkyl, C1-C6 heteroalkyl, C1-C6 aryl, and C1-C6 heteroaryl.
Dependencies are inferred from the claim text.