H. Schaeffer, E. Odin
Mar 1, 1965
Citations
0
Influential Citations
5
Citations
Journal
Journal of pharmaceutical sciences
Abstract
A series of trans -4-(6-substituted-9-purinyl) cyclohexylcarbinols were prepared by the following procedure. Ethyl p -aminobenzoate gave, on catalytic hydrogenation, trans -4-ethoxycarbonylcy clohexylamine which, on reduction with sodium and ethanol, generated trans -4-hydroxymethylcyclohexylamine. Condensation of this amine with 5-amino-4,6-dichloropyrimidine, followed by ring closure of the resultant substituted pyrimidine, gave trans -4-(6-chloro-9-purinyl) cyclohexylcarbinol (VI). Displacement of the 6-chloro group by a number of nucleophilic reagents gave a variety of nucleoside analogs. Enzymatic evaluation of these analogs established that those compounds with a 6-amino and a 6-methylamino group inhibited adenosine deaminase and that the hydroxymethyl group did not make a significant contribution to binding to the enzyme.