Fluorescent substrates for detecting organophosphatase enzyme activity

摘要

Compounds of the formula I:whereinR3 is selected from the group consisting of H, cyano, C1-C6 alkyl, C1-C6 perfluoroalkyl, C2-C6 alkenyl, C2-C6 alkynyl, aryl, and heteroaryl, formyl, carboxamide of the formula -(C=O)NR1R2 where R1 and R2 are independently H, alkyl having 1-6 carbon atoms, an aryl, or R1 and R2 taken together form a saturated 5- or 6- membered ring having the formula -(CH2)2-M-(CH2)2- where the ring moiety M is a single bond, an oxygen atom, a methylene group, or the secondary amine -NR7- where R7 is H or alkyl having 1-6 carbon atoms;R4 is selected from the group consisting of H, hydroxyl, cyano, nitro, halo, amino, amido, azido, acetal, ketal, imido, sulfo, sulfonyl, sulfinyl, sulfomethyl, salt of sulfomethyl, thiocyanato, aldehydo, keto, carbamoyl, urethane, ureido, guanidino, C1-C6 alkylamino, C1-C6 acylamino, C1-C6 alkylamido, C1-C6 alkyl, C1-C6 alkoxy, C1-C6 perfluoroalkyl, halomethyl, C1-C6 alkylthio, C5-C8 cycloalkyl, C1-C6 haloalkyl, C5-C8 halocycloalkyl, C1-C6 hydroxyalkyl, C5-C8 hydroxycycloalkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkoxycarbonyl, C2-C6 alkoxycarbonyl C1-C6 alkyl, carboxy C1-C6 alkyl, carboxy C1-C6 alkoxy, dicarboxy C1-C6 alkyl, dicarboxy C1-C6 alkoxy, C2-C6 cyanoalkyl, phosphono C1-C6 alkyl, phosphoryl C1-C6 alkyl, mono-, di-, and trisaccharides, nucleic acids, oligonucleotides, amino acids, peptides, and proteins, and C2-C6 alkenyl, C2-C6 alkynyl, aryl, arylcarbonyl, and heteroaryl, which may be optionally substituted with a substituent selected from the group consisting of hydroxyl, cyano, nitro, halo, amino, amido, azido, acetal, ketal, imido, sulfo, sulfonyl, sulfinyl, thiocyanato, aldehydo, keto, carbamoyl, urethane, ureido, and guanidine;R5 is H or C1-C6 alkoxy;R9 and R10 are ethyl;R6 and R8 are halo; andX1, X2, and X3 are independently O or S.