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), Journal Name: J. Org. Chem.; (United States) Vol. 45:12; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

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