Synthesis and chemistry of 7-amino-4-(trifluoromethyl)coumarin and its amino acid and peptide derivatives

Journal Article · Fri Jun 06 00:00:00 EDT 1980 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo01300a003· OSTI ID:7141832

Bissell, E R; Mitchell, A R; Smith, R E

The synthesis and purification of 7-amino-4-(trifluoromethyl)courmarin, 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/sup ..cap alpha../-Z-glycylglycyl-L-argininamido)-4-(trifluoromethyl)coumarins.

• Research Organization: Univ. of California, Livermore
• DOE Contract Number: W-7405-ENG-48
• OSTI ID: 7141832
• Journal Information: J. Org. Chem.; (United States), Vol. 45:12
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
COUMARIN
CHEMICAL PREPARATION
ORGANIC FLUORINE COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
EXPERIMENTAL DATA
DATA
ESTERS
HETEROCYCLIC COMPOUNDS
INFORMATION
LACTONES
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYRANS
SYNTHESIS
400301* - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)