7-hydroxy coumarins having substitutions in the 4 position

Details 7-hydroxy coumarins having substitutions in the 4 position 7-hydroxy coumarins having substitutions in the 4 position

C - Chemistry, Metallurgy

07

D

167/43, 260/356.

C07D 311/16 (2006.01) C07D 407/12 (2006.01) C07F 7/18 (2006.01) C12Q 1/68 (2006.01) G01N 33/53 (2006.01) G01N 33/58 (2006.01)

Patent

CA 2022436

Fluorescent 7-hydroxy coumarin compounds with substitutions in the 4-position and having a length greater than one carbon. More specifically, there is provided a compound of the formula: (see formula I) wherein R, is selected from the group consisting of -CH3, -G-OZ, -G-SZ, -G-NHY, -OZ, -SZ, -NHY, and alkyl of the formula -G-CH3, where G represents an alkylene chain having from 1 to 12 carbon atoms, and Z represents hydrogen or a protecting group for O or S, and Y represents hydrogen or a protecting group for N; and wherein R2 is selected from the group consisting of -J-SH, -J-X, -OH, - SH, and -COOR', where J represents an alkylene chain having from 1 to carbon atoms, X represents a halogen and R' represents H or an alkyl chain having from 1 to 10 carbon atoms. Also provided is a process for synthesis of these compounds the process comprising the steps of: a) reacting 4-bromomethyl-7-methoxycoumarin with a monoalkylated (R1) malonic ester under conditions sufficient to achieve condensation of the ester to give the monoalkylated (2-bis(carbalkoxy)-2-R1 -1-ethyl) derivative; b) removing one of the carbalkoxy groups from the product of step a); c) demethylation of the product of step b) to give the 7-hydroxycoumarin compound; and d) chemically modifying the remaining ester to yield a desired R2.

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