Research ArticleEnzyme Inhibitors VII.: Syntheses of trans-4-(6-Substituted-9-purinyl) cyclohexylcarbinols and Evaluation as Inhibitors of Adenosine Deaminase

Add time:08/24/2019    Source:sciencedirect.com

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.

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