Novel squaramide derivative and use thereof
AssigneesPusan National University Industry-University Cooperation Foundation, Kosin University Industry-Academy Cooperation
InventorsHwayoung YUN, Jee-Yeong JEONG, Jinsook KWAK, Min Jung KIM, Soyeong KIM
Life of this patent
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Abstract
The present invention relates to a novel squaramide derivative and a use thereof and provides a novel derivative through the strategy of replacing a compound having a urea core with the bioisolate squaramide, whereby the derivative exhibits an anticancer activity through eIF2α phosphorylation efficacy, wherein squaramide has a characteristic structure retaining a double bond linked to the carbonyl groups and the squaramide structure can be prepared by mediating a precursor bearing an amine group to the squarate ring, which is a squaric ring, through a conjugate addition reaction.
Claims16
A compound selected from a squaramide derivative compound represented by the following Chemical Formula 1, a pharmaceutically acceptable salt thereof, a solvent thereof, or a stereoisomer thereof:
- wherein in the Chemical Formula 1,
- R1, R2, and R4 are the same or different respectively and selected from the group consisting of hydrogen (H), hydroxy (OH), halogen, trifluoromethyl (CF3), (C1˜C4)alkyl, (C1˜C4)alkoxy, and acetate (COOMe),
- R3 is selected from the group consisting of hydrogen (H) and cyano (CN), and
- R5 is selected from the group consisting of trifluoromethyl group (CF3), cyano (CN), nitrite (NO2), (C1˜C4)alkylsulfonyl (SO2Me), and aminosulfonyl (SO2NH2), except that:
- i) R1 is tert-butyl, R2, R3 and R4 are hydrogen (H), and R5 is methylsulfonyl (SO2Me), and
- ii) R1 is trifluoromethyl (CF3), R2 and R4 are hydrogen (H), R3 is cyano (CN), and
- R5 is trifluoromethyl (CF3).
5-12. (canceled)
A method of preventing or treating cancer, comprising:
- administering a pharmaceutical composition comprising a compound as an active ingredient to a subject, the compound selected from a squaramide derivative compound represented by the following Chemical Formula 1, a pharmaceutically acceptable salt thereof, a solvent thereof, or a stereoisomer thereof:
- wherein in the Chemical Formula 1,
- R1, R2, and R4 are the same or different respectively and selected from the group consisting of hydrogen (H), hydroxy (OH), halogen, trifluoromethyl (CF3), (C1˜C4)alkyl, (C1˜C4)alkoxy, and acetate (COOMe),
- R3 is selected from the group consisting of hydrogen (H) and cyano (CN), and
- R5 is selected from the group consisting of trifluoromethyl group (CF3), cyano (CN), nitrite (NO2), (C1˜C4)alkylsulfonyl (SO2Me), and aminosulfonyl (SO2NH2), except that:
- i) R1 is tert-butyl, R2, R3 and R4 are hydrogen (H), and R5 is methylsulfonyl (SO2Me), and
- ii) R1 is trifluoromethyl (CF3), R2 and R4 are hydrogen (H), R3 is cyano (CN), and
- R5 is trifluoromethyl (CF3).
A method of inhibiting cancer cell metabolism, comprising:
- administering a pharmaceutical composition comprising a compound as an active ingredient to a subject, the compound selected from a squaramide derivative compound represented by the following Chemical Formula 1, a pharmaceutically acceptable salt thereof, a solvent thereof, or a stereoisomer thereof:
- wherein in the Chemical Formula 1,
- R1, R2, and R4 are the same or different respectively and selected from the group consisting of hydrogen (H), hydroxy (OH), halogen, trifluoromethyl (CF3), (C1˜C4)alkyl, (C1˜C4)alkoxy, and acetate (COOMe),
- R3 is selected from the group consisting of hydrogen (H) and cyano (CN), and
- R5 is selected from the group consisting of trifluoromethyl group (CF3), cyano (CN), nitrite (NO2), (C1˜C4)alkylsulfonyl (SO2Me), and aminosulfonyl (SO2NH2), except that:
- i) R1 is tert-butyl, R2, R3 and R4 are hydrogen (H), and R5 is methylsulfonyl (SO2Me), and
- ii) R1 is trifluoromethyl (CF3), R2 and R4 are hydrogen (H), R3 is cyano (CN), and
- R5 is trifluoromethyl (CF3).
Dependencies are inferred from the claim text.