Research ArticleEnzyme Inhibitors III: Syntheses of cis-(6-Substituted-9-purinyl) cycloalkylcarbinols as Adenosine Deaminase Inhibitors

Add time:08/23/2019    Source:sciencedirect.com

The syntheses of cis-4-(6-chloro-9-purinyl)cyclohexylcarbinol (VI) and cis-3-(6-chloro-9-purinyl)cyclopentylcarbinol (XVII) have been accomplished by the condensation of 5-amino-4,6-dichloropyrimidine with the appropriate amino alcohol, followed by ring closure of the resultant substituted pyrimidine to give the desired purines. Nucleophilic displacement of the 6-chloro group in VI and XVII gave the following 6-substituted derivatives: (a) hydroxy, (b) mercapto, (c) amino, (d) methylamino, and (e) dimethylamino. Evaluation of these substrate analogs as inhibitors of adenosine deaminase revealed that those compounds with an amino or methylamino group at the 6-position of the purine nucleus were inhibitory and that the hydroxymethyl group on the cyclopentyl or cyclohexyl nucleus makes only a small contribution to binding of the inhibitor to the enzyme.

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