Derivatives of 6,8-difluoro-7-hydroxycoumarin

Details Derivatives of 6,8-difluoro-7-hydroxycoumarin Derivatives of 6,8-difluoro-7-hydroxycoumarin

C - Chemistry, Metallurgy

07

D

C07D 311/18 (2006.01) C07C 47/565 (2006.01) C07C 49/825 (2006.01) C07D 311/16 (2006.01) C07D 311/42 (2006.01) C07D 311/54 (2006.01) C07D 405/02 (2006.01) C07D 413/04 (2006.01) C07D 417/04 (2006.01) C07F 5/02 (2006.01) C07F 9/655 (2006.01) C07H 15/26 (2006.01) C07H 21/00 (2006.01) C08B 37/00 (2006.01) C09B 57/02 (2006.01) C12Q 1/00 (2006.01) C12Q 1/28 (2006.01) C12Q 1/34 (2006.01) C12Q 1/42 (2006.01) C12Q 1/68 (2006.01) G01N 33/52 (2006.01) G01N 33/533 (2006.01)

Patent

CA 2219648

ABSTRACT Compounds of the formula Image wherein R3 is H, C1-C18 alkyl, C1-C18 perfluoroalkyl, CN, formyl, aryl, heteroaryl, arylcarbonyl, or -(C=O)-NR1R2 where R1 and R2 are independently H, C1-C6 alkyl, aryl, or R1 and R2 taken in combination are -(CH2)2-M-(CH2)2- where M is a single bond, -O-, -CH2-, or - NR6-, where R6 is H or C1-C6 alkyl; or R3 is -L-RX or -L-SC; R4 is H, OH, CN, C1-C18 alkyl, C1-C18 perfluoroalkyl, sulfomethyl, biologically compatible salt of sulfomethyl, halomethyl, aryl, -L-R X or -L-S C; R5 is H or C1-C6 alkoxy; R7 is H, or a monovalent moiety derived by removal of a hydroxy group from a phosphate, a thiophosphate, a sulfate, or a biologically compatible salt thereof; or a monovalent moiety derived by removal of a hydroxy group from a carboxy group of an aliphatic or aromatic carboxylic acid; or a monovalent moiety derived by removal of a hydroxy group from an alcohol or from a mono- or polysaccharide; or R7 is a photolabile caging group; wherein aryl is an aromatic substituent having 6 conjugated carbon atoms that is optionally and independently substituted by H, halogen, cyano, sulfo, biologically compatible salts of sulfo, carboxy, nitro, alkyl, perfluoroalkyl, alkoxy, alkylthio, amino, monoalkylamino, dialkylamino or alkylamido; heteroaryl is a 5- or 6-membered aromatic heterocycle that is optionally fused to additional six-membered aromatic ring or is fused to one 5- or 6-membered heteroaromatic ring, said heteroaromatic rings containing at least 1 and as many as 3 heteroatoms that are selected from the group consisting of O, N and S in any combination, that is attached by a single bond, and is optionally and independently substituted by H, halogen, C1-C6 alkyl, or C1-C6 alkoxy; each L is independently a single covalent bond, or L is a covalent linkage having 0-24 nonhydrogen atoms selected from the group consisting of C, N, O and S and is composed of any combination of single, double, triple or aromatic carbon-carbon bonds, carbon- nitrogen bonds, nitrogen-nitrogen bonds, carbon-oxygen bonds and carbon-sulfur bonds; R X is a reactive group; and S C is a conjugated substance are fluorescent dyes which typically possess greater photostability and lower pH sensitivity in the physiological pH range than their nonfluorinated analogs, exhibit less fluorescence quenching when conjugated to a substance, possess absorption and emission spectra that closely match those of their nonfluorinated analogs, and also exhibit higher quantum yields than their nonfluorinated analogs.

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