H. Schaeffer, D. D. Godse, G. Liu
Dec 1, 1964
Citations
0
Influential Citations
14
Citations
Journal
Journal of pharmaceutical sciences
Abstract
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.