New nucleoside analogs from 2-amino-9-(beta-D-ribofuranosyl)purine.
Four novel derivatives of 2-amino-9-(beta-D-ribofuranosyl)purine (1) were synthesised and fully characterised. When 1 was reacted with chloroacetaldehyde (a), 2-chloropropanal (b), bromomalonaldehyde (c) and a mixture of chloroacetaldehyde + malonaldehyde (d), 3-(beta-D-ribofuranosyl)-imidazo-[1,2a]purine (2), 3-(beta-D-ribofuranosyl)-5-methylimidazo-[1,2a]purine (3), 3-(beta-D-ribofuranosyl)-5-formylimidazo-[1,2a]purine (4) and 9-(beta-D-ribofuranosyl)-2-(3,5-diformyl-4-methyl-1,4-dihydro-1-pyridyl)purine (5) were formed, respectively. The products were isolated, purified by chromatography and characterised by MS, complete NMR assignment as well as fluorescence and UV spectroscopy. The yields of these reactions were moderate (14-20%). The fluorescence properties differed from those of the starting compound and the quantum yields were considerably lower.
Abo Akademi University, Department of Organic Chemistry, Biskopsgatan 8, FIN-20500 Turku/Abo, Finland. piritta.virta@abo.fi
Piritta
P
Virta
Toni
T
Holmström
Mattias U
MU
Roslund
Peter
P
Mattjus
Leif
L
Kronberg
Rainer
R
Sjöholm
D004355:Drug Stability; D006863:Hydrogen-Ion Concentration; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D013057:Spectrum Analysis
C502517:2-amino-9-(beta-D-ribofuranosyl)purine; D009705:Nucleosides