Facile synthesis of 9-substituted 9-deazapurines as potential purine nucleoside phosphorylase inhibitors.
A facile synthesis of 9-substituted 9-deazapurines as potential inhibitors of purine nucleoside phosphorylase has been achieved by the direct Friedel-Crafts aroylation or arylmethylation of 9-deazapurines using trifluoromethanesulfonic acid as catalyst. The aroylated 9-deazapurines could be transformed into the corresponding 9-aryimethyl derivatives by the Wolff-Kishner reaction. A novel synthesis of 9-deazahypoxanthine was also developed by treatment of 4-hydroxy-5-phenylazo-6-methylpyrimidin-2-thione with triethyl orthoformate in trifluoroacetic acid (TFA) to yield 8-oxo-7H-2-phenylpyrimido[5,4-c]pyridazin-6-thione followed by Raney nickel reduction.
Shih
Hsiencheng
H
Department of Medicine and The Sam and Rose Stein Institute for Research on Aging, University of California, San Diego, La Jolla 92093-0663, USA. hshih@ucsd.edu
Cottam
Howard Brinkerhoff
HB
Carson
Dennis Anthony
DA
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D011683:Purine-Nucleoside Phosphorylase / Q000037:antagonists & inhibitors*; D011687:Purines / Q000138:chemical synthesis* / Q000494:pharmacology
D004791:Enzyme Inhibitors; D011687:Purines; D011683:Purine-Nucleoside Phosphorylase