R. H. Shah, H. Schaeffer, D. H. Murray
1965
Citations
0
Influential Citations
18
Citations
Journal
Journal of pharmaceutical sciences
Abstract
A series of 6-substituted-9-(5-deoxy- β -D-xylofuranosyl)purines was prepared by the following procedure. D-Xylose was converted by an eight-step reaction sequence into 2-acetyl-3-benzoyl-5-deoxy-D-xylofuranosyl chloride (VI) which, on condensation with chloromercuri-6-chloropurine, gave 6-chloro-9-(2-acetyl-3-benzoyl-5-deoxy- β -D-xylofuranosyl)purine (VIII). Displacement of the 6-chloro group in VIII, followed by removal of the blocking groups, gave the following 6-substituted nucleosides: ( a ) amino, ( b ) methylamino, ( c ) dimethylamino, ( d ) mercapto, ( e ) methoxy, ( f ) hydrogen. Those nucleosides with a 6-amino, 6-methylamino, 6-dimethylamino, and 6-methoxy group inhibited, to a varying degree, the enzyme adenosine deaminase. In addition, the 6-amino analog was a substrate of adenosine deaminase.