Syntheses of highly functionalised 6-substituted pteridines.
Methods for the synthesis of polyfunctional 6-substituted pteridines from the corresponding 6-aldehydes are described. Alkene, ester, ketone, amide, cyano, oxime, bromo, methoxy and dihydroxy functional groups have all been introduced principally through improved methodologies for Wittig reactions using 2-thioalkyl-6-formylpteridines as substrates. Further modification of the alkenes derived from the Wittig reactions was difficult but selective conversion to the vic-diol was possible using ligand assisted catalysis with osmium tetraoxide. These methods are a component of an extensive methodology for the preparation of compounds that might serve as modulators of tetrahydrobiopterin activity or as inhibitors of dihydroneopterin aldolase.
Guiney
Donie
D
Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK G1 1XL.
Gibson
Colin L
CL
Suckling
Colin J
CJ
D000446:Aldehyde-Lyases / Q000037:antagonists & inhibitors; D000447:Aldehydes / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D011621:Pteridines / Q000138:chemical synthesis*
D000447:Aldehydes; D004791:Enzyme Inhibitors; D011621:Pteridines; D000446:Aldehyde-Lyases; C020044:dihydroneopterin aldolase