S. Boiadjiev, Zachary R. Woydziak, A. Mcdonagh
Jul 17, 2006
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0
Influential Citations
9
Citations
Journal
Tetrahedron
Abstract
Abstract From non-fluorescent 8- H fluorophenyldipyrrinones, highly fluorescent ( ϕ F 0.4–0.6) analogs have been synthesized by reaction with 1,1′-carbonyldiimidazole to bridge the dipyrrinone nitrogens and form an N , N ′-carbonyldipyrrinone (3 H ,5 H -dipyrrolo[1,2- c :2′,1′- f ]pyrimidine-3,5-dione). Amphiphilic, water-soluble 8-sulfonic acid derivatives are then obtained by reaction with concd H 2 SO 4 . The resulting fluorinated and sulfonated N , N ′-carbonyl-bridged dipyrrinones, isolated as their sodium salts, are potential cholephilic fluorescence and 19 F MRI imaging agents for use in probing liver and biliary metabolism. After intravenous injection in the rat they were excreted rapidly and largely unchanged in bile. 19 F NMR spectroscopy of a pentafluorophenyl-tosylpyrrolinone synthetic precursor exhibited rarely seen diastereotopicity.