Synthesis and Chemistry of 7-Amino-4-(trifluoromethyl)coumarin and Its Amino Acid and Peptide Derivatives

Article abstract of DOI:10.1021/jo01300a003

The synthesis and purification of 7-amino-4-(trifluoromethyl)coumarin, a novel fluorescent marker for the sensitive detection of proteinases, were investigated.Two byproducts, 7-hydroxy-4-(trifluoromethyl-2-quinolone and 2-ethoxy-7-hydroxy-4-(trifluoromethyl)quinoline, were isolated and identified. 7-Methoxy-4-(trifluoromethyl)-2-quinolone was also prepared.Amino acid and peptide derivatives prepared by solution methods using the stepwise approach included 7-(L-leucinamido)-, 7-(D-alanyl-L-leucyl-L-lysinamido)-, 7-(D-valyl-L-leucyl-L-lysinamido)-, and 7-(N^α-Z-glycylglycyl-L-argininamido)-4-(trifluoromethyl)coumarins